Accoun ts Letters - Thieme Chemistry
Accoun ts Letters - Thieme Chemistry
Accoun ts Letters - Thieme Chemistry
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1181<br />
Insoluble Polymer-Bound (IPB) Approach to the<br />
Catalytic Asymmetric Dihydroxylation of Alkenes<br />
P. Salvadori, D. Pini, A. Petri<br />
1191<br />
Iodocarbocyclization and Iodoaminocyclization<br />
Reactions Mediated by a Metallic Reagent<br />
O. Kitagawa, T. Taguchi<br />
1200<br />
Facile Acetylation of Alcohols, Ethers and Ketals<br />
with Catalytic FeCl3 in AcOH<br />
G. V. M. Sharma*, A. K. Mahalingam, M. Nagarajan, A. Ilangovan,<br />
P. Radhakrishna<br />
1203<br />
Preparation of Non-Symmetrical 2,3-Bis-(2,2’-oligopyridyl)pyrazines<br />
via 1,2-Disubstituted Ethanones<br />
F. R. Heirtzler<br />
1207<br />
Copper(II) Pivalate/Oxone: An Improved Promoter<br />
System for Aryl Transfer via Organo-Bismuth<br />
Reagen<strong>ts</strong><br />
G. S. Sheppard<br />
<strong>Accoun</strong><strong>ts</strong> and<br />
Rapid Communications in<br />
Synthetic Organic <strong>Chemistry</strong><br />
R 1<br />
NuH MLn ( ) n<br />
Me<br />
N CO2R3 n<br />
NuMLn-1 ( ) n I2<br />
"activation of nucleophile"<br />
"control of selectivity "<br />
N<br />
m<br />
R 2<br />
N<br />
N<br />
I<br />
N<br />
N R1 m<br />
n<br />
1999<br />
No. 8<br />
August<br />
( )n<br />
R 2<br />
Nu<br />
<strong>Accoun</strong><strong>ts</strong><br />
<strong>Letters</strong>
<strong>Letters</strong><br />
IV Table of Conten<strong>ts</strong><br />
1211<br />
Kinetic and Thermodynamic Control in the<br />
Synthesis of Tetrahydro-Pyrans and -Furans from<br />
1,4-Diols by Stereospecific Phenylsulfanyl (PhS)<br />
Migration: Competition Between exo and endo<br />
Transition States and between [1,2] and [1,4]<br />
Sulfanyl Participation<br />
J. Eames, N. Kuhnert, F. H. Sansbury, S. Warren<br />
1215<br />
[1,4]-SPh Shift Cyclisations or [1,2]-SPh-Cyclisations<br />
as Alternative Cascade Sequences for Stereocontrolled<br />
Synthesis of Substituted Tetrahydrofurans<br />
J. Eames, N. Kuhnert, S. Warren<br />
1219<br />
Synthesis of a Polyhydroxyquinolizidine bearing a<br />
Polyhydroxylated Carbon Side-Chain<br />
C. Schaller, P. Vogel<br />
1223<br />
Palladium-Catalyzed Synthesis of N-Aryl- and N-<br />
Heteroaryl-aza-crown Ethers via Cross-Coupling<br />
Reactions of Aryl- and Heteroaryl Bromides with<br />
Aza-crown Ethers<br />
B. Witulski<br />
1227<br />
First Synthesis of Xerulin, an Inhibitor of the<br />
Biosynthesis of Cholesterol<br />
K. Siegel, R. Brückner<br />
1231<br />
Oxidative Asymmetrization of Racemic Alkenes:<br />
Asymmetric Synthesis of Optically Active Dicyclopentadiene<br />
Derivatives<br />
Y. Kohmura, T. Ka<strong>ts</strong>uki<br />
O<br />
Ph3P<br />
+<br />
(4 eq)<br />
O<br />
O<br />
H<br />
H<br />
1) PhCO3Bu-t (1 eq)<br />
Cu(OTf)2-L* (0.05 eq)<br />
2) NaOHaq O<br />
O<br />
H<br />
H<br />
HO<br />
(racemic)<br />
L* = chiral tris(oxazoline) ligand<br />
80% ee, 27%<br />
O<br />
O<br />
O<br />
O
Table of Conten<strong>ts</strong> V<br />
1235<br />
Formation of Four-Membered Rings Using the<br />
Intramolecular Wittig Reaction: Convenient<br />
Generation of Functionalised Butadienes<br />
R. A. Aitken, M. E. Balkovich, H. J. Bestmann, O. Clem,<br />
S. E. Gibson, T. Röder<br />
1237<br />
A Convenient and Practical Route to Novel a-Allenic<br />
Ketones through a Wittig Reaction<br />
K. Kumar, S. Kaur, M. P. S. Ishar<br />
1239<br />
The Synthesis of Aminoazole Analogs of Lysine and<br />
Arginine: The Mi<strong>ts</strong>unobu Reaction with Lysinol and<br />
Argininol<br />
H.-O. Kim, M. Kahn<br />
1241<br />
A Concise Synthesis of 3-Hydroxy-4-(b-glucopyranosyl)<br />
Benzoate: A New Route to b-C-Aryl<br />
Glycosides<br />
C. Fuganti, S. Serra<br />
1243<br />
Formal Protection of Vinylepoxides via Stereospecific<br />
Chlorohydrin Formation<br />
N. Daviu, A. Delgado, A. Llebaria<br />
1245<br />
A Convenient New Method for the Bromination of<br />
Deactivated Aromatic Compounds<br />
J. Duan, L. H. Zhang, W. R. Dolbier, Jr.<br />
Ph 3P<br />
O<br />
OR 1<br />
O R 2<br />
R 1 O<br />
R 2<br />
O<br />
R 1 O<br />
O<br />
R 2<br />
<strong>Letters</strong>
<strong>Letters</strong><br />
VI Table of Conten<strong>ts</strong><br />
1247<br />
Deprotection of Tetrahydropyranyl Ethers with<br />
Montmorillonite K-10 Clay in Methanol<br />
T. Taniguchi, K. Kadota, A. S. ElAza, K. Ogasawara<br />
1249<br />
a-Keto Esters as Electrophiles for the Chalcogeno-<br />
Baylis-Hillman Reaction<br />
D. Basavaiah, K. Muthukumaran, B. Sreenivasulu<br />
1251<br />
Microwave Assisted Synthesis of Pyrrolo[2,1c][1,4]benzodiazepine-5,11-diones<br />
A. Kamal, B. S. N. Reddy, G. S. K. Reddy<br />
1253<br />
1,4-Addition Reactions of Bis(iodozincio)methane<br />
with a,b-Unsaturated Ketones<br />
S. Ma<strong>ts</strong>ubara, D. Arioka, K. Utimoto<br />
1255<br />
Esterification of Carboxylic Acids with Alcohols by<br />
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium<br />
Chloride (DMTMM)<br />
M. Kunishima, J. Morita, C. Kawachi, F. Iwasaki, K. Terao,<br />
S. Tani<br />
1257<br />
Diastereoselective Oxyselenylation of 1,n-Diolefins<br />
Utilizing PET Generated [PhSeSePh] +. as an Electrophilic<br />
Species: An Efficient and General Strategy<br />
for the Synthesis of a,a’-trans-Dialkyl Cyclic Ethers<br />
G. Pandey, R. Sochanchingwung, S. K. Tiwari<br />
R 1<br />
O<br />
OH<br />
+<br />
MeO<br />
N<br />
MeO<br />
N<br />
N<br />
N<br />
+ Me<br />
O<br />
Cl- DMTMM<br />
MeN<br />
R2OH rt<br />
O<br />
R 1<br />
O<br />
OR 2
Table of Conten<strong>ts</strong> VII<br />
1259<br />
Unexpected Switching between Addition and Substitution<br />
in the Rhodium-Catalysed Reaction between<br />
Tin Hydrides and Propargyl Ethers<br />
T. N. Mitchell, S.-N. Moschref<br />
1261<br />
Lithium Tetrafluoroborate-in Acetonitrile ( LTAN )<br />
Catalyzed Ferrier Rearrangement – Facile Synthesis<br />
of Alkyl 2,3-Unsaturated Glycopyranosides<br />
B Sobhana Babu, K. K. Balasubramanian<br />
1263<br />
First Synthesis of 1-Phenyl-3-pyrrol-1-ylindan-2carboxylic<br />
Acid, a New Scaffold of Potential Nonpeptide<br />
Endothelin Receptor Antagonis<strong>ts</strong><br />
J. Guillon, P. Dallemagne, S. Stiebing, P. R. Bovy, S. Rault<br />
1265<br />
Iminophosphoranes in Heterocyclic <strong>Chemistry</strong>.<br />
A Simple One-Pot Synthesis of Dihydropyrimidines<br />
and Pyrimidines<br />
E. Rossi, G. Abbiati, E. Pini<br />
1268<br />
A Practical Transformation of Aldehydes into (E)-<br />
Iodoalkenes with Geminal Dichromium Reagen<strong>ts</strong><br />
K. Takai, T. Ichiguchi, S. Hikasa<br />
1271<br />
A New Synthesis of Pyrrole-2-Carboxylic Acids<br />
C. S. Pak, M. Nyerges<br />
<strong>Letters</strong>
<strong>Letters</strong><br />
VIII Table of Conten<strong>ts</strong><br />
1274<br />
A Facile Synthesis of 3’-Deoxy-3’-fluorothymidine<br />
via a Highly Stereoselective Glycosylation with 2,3-<br />
Dideoxy-3-fluoro-D-erythro-pentofuranosyl Diethyl<br />
Phosphite<br />
J. Inagaki, H. Sakamoto, M. Nakajima, S. Nakamura,<br />
S. Hashimoto<br />
1277<br />
Polymer-Supported Acid Catalyst in the Carbon-<br />
Carbon Bond Formation of Acetals with Silylated<br />
Nucleophiles<br />
N. Tanaka, Y. Masaki<br />
1280<br />
Treatment of N-Boc Derivatives of b-Amino Alcohols<br />
with N,N-Diethylaminosulfur Trifluoride Leads to<br />
Chiral Oxazolidinones: An Unexpected Intramolecular<br />
Cyclization<br />
H. Zhao, A. Thurkauf<br />
1283<br />
A New and Extremely Active Corey’s Chiral Oxazaborolidine<br />
Catalyst<br />
K. Ishihara, S. Kondo, H. Yamamoto<br />
1286<br />
Sulfur-Controlled Exo Selective Aryl Radical<br />
Cyclization onto Exo-Methylenecycloalkanes<br />
H. Ishibashi, T. Kobayashi, D. Takamasu<br />
1289<br />
A Novel Carbocyclic Ring Closure of Hex-5enopyranosides<br />
and Pent-4-enofuranosides<br />
J. K. Gallos, T. V. Koftis, A. E. Koumbis, V. I. Mou<strong>ts</strong>os<br />
OTMS<br />
O<br />
N<br />
Me<br />
HN<br />
Me<br />
BzO<br />
O<br />
TMSO N<br />
(1.5 equiv.)<br />
BzO<br />
F<br />
OP(OEt)2 TMSOTf (1.0 equiv.)<br />
EtCN, -50 °C, 30 min<br />
α:β=64:36<br />
R OMe<br />
OMe<br />
(50 mg)<br />
NC<br />
NC<br />
O<br />
O<br />
N<br />
O Ot DAST<br />
CH2F Bu<br />
O<br />
O<br />
O<br />
O<br />
polymer cat. (50 mg), TMS-Nu (1.5 eq.)<br />
CH 3CN, reflux<br />
R = aryl, aliphatic, α,β-unsaturated<br />
Nu = CN, CH2COPh, CH2CO-2-Furyl<br />
N<br />
O Ot CH2OH DAST<br />
Bu<br />
SPh PhS<br />
Br<br />
Bu3SnH AIBN<br />
( )n<br />
( ) n<br />
O<br />
O<br />
N<br />
F<br />
β:α=91:9<br />
R OMe<br />
Nu<br />
N O<br />
O
Table of Conten<strong>ts</strong> IX<br />
1292<br />
Highly Enantioselective Synthesis of Substituted<br />
Piperidines using the Chiral Lithium Amide Base<br />
Approach<br />
N. J. Goldspink, N. S. Simpkins, M. Beckmann<br />
1295<br />
<strong>Chemistry</strong> of Insect Antifeedan<strong>ts</strong> from Azadirachta<br />
indica (Part 22): Functionalisation of the Decalin<br />
Fragment of Azadirachtin via a Claisen Rearrangement<br />
Reaction<br />
S. V. Ley, C. E. Gutteridge, A. R. Pape, C. D. Spilling,<br />
C. Zumbrunn<br />
1298<br />
The Baker’s Yeast Reduction of the b-Keto Aldehydes<br />
in the Presence of a Sulfur Compound<br />
R. Hayakawa, M. Shimizu<br />
1301<br />
N-Carboalkoxy-2-Nitrobenzenesulfonamides:<br />
A Practical Preparation of N-Boc-, N-Alloc-, and<br />
N-Cbz-Protected Primary Amines<br />
T. Fukuyama, M. Cheung, T. Kan<br />
1304<br />
Triazenes: A Useful Protecting Strategy for Sensitive<br />
Secondary Amines<br />
R. Lazny, J. Poplawski, J. Köbberling, D. Enders, S. Bräse<br />
1307<br />
Diastereoselectivity in Michael Additions to a<br />
Pyrrolidinyl Enone<br />
R. W. Bates, P. Kongsaeree<br />
MeO2C<br />
TESO<br />
MeO2C R 1<br />
N CO2Me<br />
Bn<br />
H<br />
O<br />
Ph<br />
MeO2C TESO<br />
O OBnR2<br />
O<br />
Ph<br />
N<br />
Li<br />
Ph<br />
N<br />
Li Ph<br />
THF, -78 °C<br />
electrophile<br />
(≥ 98% ee)<br />
R 1<br />
O OH<br />
H<br />
R2 R1 O<br />
OH<br />
R2 R1 OH<br />
R2 Baker's Yeast<br />
Sulfur-Compound<br />
N<br />
O Ot DAST<br />
CH2F Bu<br />
∆<br />
MeO 2C<br />
TESO<br />
MeO2C H<br />
O<br />
N CO2Me<br />
Bn E<br />
MeO2C<br />
TESO<br />
O OBn<br />
R2 R<br />
OH<br />
1<br />
N<br />
O Ot CH2OH DAST<br />
Bu<br />
OH<br />
R 2<br />
O<br />
OH<br />
N O<br />
O<br />
R 1<br />
<strong>Letters</strong>
<strong>Letters</strong><br />
X Table of Conten<strong>ts</strong><br />
1310<br />
Improved Method for the Preparation of<br />
Macrocyclic Diamides<br />
D. T. Gryko, D. Gryko, J. Jurczak<br />
1313<br />
Stereoselective Conjugate Addition of Alkyl Groups<br />
to (S)-4-(tert-Butyldimethylsilyloxy)-2-phenylsulfonyl-2-cyclopentenone<br />
by Means of Trialkylaluminum<br />
Reagen<strong>ts</strong><br />
T. Yakura, K. Tanaka, M. Iwamoto, M. Nameki, M. Ikeda<br />
1316<br />
A New Route to L-Iduronate Building-blocks for the<br />
Synthesis of Heparin-like Oligosaccharides<br />
R. Ojeda, J. L. de Paz, M. Martín-Lomas, J. M. Lassaletta<br />
1319<br />
Novel Axial Chiral Sulfur-oxazoline Ligands with a<br />
Biphenyl Backbone<br />
Y. Imai, W. Zhang, T. Kida, Y. Naka<strong>ts</strong>uji, I. Ikeda<br />
1322<br />
A Concise Route to Carbasugars<br />
Y. Le Merrer, C. Gravier-Pelletier, W. Maton, M. Numa,<br />
J.-C. Depezay<br />
1325<br />
Synthetic Studies towards Mniopetals (I). A Short<br />
Synthesis of a Key Intermediate for the Total<br />
Synthesis of Mniopetals<br />
J. Jauch<br />
O<br />
O<br />
S<br />
H2N OMe<br />
+<br />
OMe<br />
TBDMSO<br />
HO<br />
O<br />
O<br />
H 2N<br />
O<br />
O<br />
O<br />
O<br />
O<br />
MeOH, NaOMe<br />
48 h<br />
O<br />
NH<br />
O<br />
S<br />
HN<br />
O<br />
57%<br />
O<br />
O<br />
O<br />
NH<br />
O<br />
HN<br />
O<br />
+ S<br />
S<br />
O<br />
NH<br />
O<br />
HN<br />
O<br />
O<br />
O<br />
TBDMSO R<br />
10%<br />
SO2Ph R3Al SO2Ph toluene<br />
OBn<br />
O<br />
MeO2C O<br />
5 Steps, 17% overall<br />
R<br />
N M<br />
SR' M RS'<br />
N<br />
R M<br />
O<br />
O<br />
(S,aS )<br />
3<br />
M=PdCl2<br />
RS'<br />
O O<br />
H H<br />
M<br />
(S,aR)<br />
not found<br />
Up to 82% ee was attained in palladium-catalyzed allylic<br />
alkylation.<br />
N<br />
O<br />
R<br />
OTDS<br />
PO OP<br />
PO<br />
PO<br />
O<br />
*<br />
OP<br />
+<br />
*<br />
O<br />
S S<br />
Si<br />
SiO<br />
*<br />
S<br />
*<br />
S<br />
OH SiO<br />
+<br />
*<br />
S<br />
*<br />
S<br />
OP<br />
OH<br />
Si = TBDMS
Table of Conten<strong>ts</strong> XI<br />
1328<br />
Organic Synthesis Supported by Antibody Catalysis<br />
J. Hasserodt<br />
1339<br />
Indium<br />
Compiled by Dramane Lainé<br />
Errata 1340<br />
New Tools<br />
in Synthesis<br />
Synlett<br />
Spotlight
XII Table of Conten<strong>ts</strong><br />
Author Index<br />
Abbiati, G. 1265<br />
Aitken, R. A. 1235<br />
Arioka, D. 1253<br />
Balasubramanian, K. K. 1261<br />
Balkovich, M. E. 1235<br />
Basavaiah, 1249<br />
Bates, R. W. 1307<br />
Beckmann, M. 1292<br />
Bestmann, H. J. 1235<br />
Bovy, P. R. 1263<br />
Bräse, S. 1304<br />
Brückner, R. 1227<br />
Cheung, M. 1301<br />
Clem, O. 1235<br />
Dallemagne, P. 1263<br />
Daviu, N. 1243<br />
de Paz, J. L. 1316<br />
Delgado, A. 1243<br />
Depezay, J.-C. 1322<br />
Dolbier, Jr., W. R. 1245<br />
Duan, J. 1245<br />
Eames, J. 1211, 1215<br />
ElAza, A. S. 1247<br />
Enders, D. 1304<br />
Fuganti, C. 1241<br />
Fukuyama, T. 1301<br />
Gallos, J. K. 1289<br />
Gibson, S. E. 1235<br />
Goldspink, N. J. 1292<br />
Gravier-Pelletier, C. 1322<br />
Gryko, D. 1310<br />
Gryko, D. T. 1310<br />
Guillon, J. 1263<br />
Gutteridge, C. E. 1295<br />
Hashimoto, S. 1274<br />
Hasserodt, J. 1328<br />
Hayakawa, R. 1298<br />
Heirtzler, F. R. 1203<br />
Hikasa, S. 1268<br />
Ichiguchi, T. 1268<br />
Ikeda, I. 1319<br />
Ikeda, M. 1313<br />
Ilangovan, A. 1200<br />
Imai, Y. 1319<br />
Inagaki, J. 1274<br />
Ishar, M. P. S. 1237<br />
Ishibashi, H. 1286<br />
Ishihara, K. 1283<br />
Iwamoto, M. 1313<br />
Iwasaki, F. 1255<br />
Jauch, J. 1325<br />
Jurczak, J. 1310<br />
Kadota, K. 1247<br />
Kahn, M. 1239<br />
Kamal, A. 1251<br />
Kan, T. 1301<br />
Ka<strong>ts</strong>uki, T. 1231<br />
Kaur, S. 1237<br />
Kawachi, C. 1255<br />
Kida, T. 1319<br />
Kim, H.-O. 1239<br />
Kitagawa, O. 1191<br />
Kobayashi, T. 1286<br />
Köbberling, J. 1304<br />
Koftis, T. V. 1289<br />
Kohmura, Y. 1231<br />
Kondo, S. 1283<br />
Kongsaeree, P. 1307<br />
Koumbis, A. E. 1289<br />
Kuhnert, N. 1211, 1215<br />
Kumar, K. 1237<br />
Kunishima, M. 1255<br />
Lainé, D. 1339<br />
Lassaletta, J. M. 1316<br />
Lazny, R. 1304<br />
Le Merrer, Y. 1322<br />
Ley, S. V. 1295<br />
Llebaria, A. 1243<br />
Mahalingam, A. K. 1200<br />
Martín-Lomas, M. 1316<br />
Masaki, Y. 1277<br />
Maton, W. 1322<br />
Ma<strong>ts</strong>ubara, S. 1253<br />
Mitchell, T. N. 1259<br />
Morita, J. 1255<br />
Moschref, S.-N. 1259<br />
Mou<strong>ts</strong>os, V. I. 1289<br />
Muthukumaran, K. 1249<br />
Nagarajan, M. 1200<br />
Nakajima, M. 1274<br />
Nakamura, S. 1274<br />
Naka<strong>ts</strong>uji, Y. 1319<br />
Nameki, M. 1313<br />
Numa, M. 1322<br />
Nyerges, M. 1271<br />
Ogasawara, K. 1247<br />
Ojeda, R. 1316<br />
Pak, C. S. 1271<br />
Pandey, G. 1257<br />
Pape, A. R. 1295<br />
Petri, A. 1181<br />
Pini, D. 1181<br />
Pini, E. 1265<br />
Poplawski, J. 1304<br />
R. Lazny et al. 1304<br />
Radhakrishna, P. 1200<br />
Rault, S. 1263<br />
Reddy, B. S. N. 1251<br />
Reddy, G. S. K. 1251<br />
Röder, T. 1235<br />
Rossi, E. 1265<br />
Sakamoto, H. 1274<br />
Salvadori, P. 1181<br />
Sansbury, F. H. 1211<br />
Schaller, C. 1219<br />
Serra, S. 1241<br />
Sharma, G. V. M. 1200<br />
Sheppard, G. S. 1207<br />
Shimizu, M. 1298<br />
Siegel, K. 1227<br />
Simpkins, N. S. 1292<br />
Sobhana Babu, B 1261<br />
Sochanchingwung, R. 1257<br />
Spilling, C. D. 1295<br />
Sreenivasulu, B. 1249<br />
Stiebing, S. 1263<br />
Taguchi, T. 1191<br />
Takai, K. 1268<br />
Takamasu, D. 1286<br />
Tanaka, K. 1313<br />
Tanaka, N. 1277<br />
Tani, S. 1255<br />
Taniguchi, T. 1247<br />
Terao, K. 1255<br />
Thurkauf, A. 1280<br />
Tiwari, S. K. 1257<br />
Utimoto, K. 1253<br />
Vogel, P. 1219<br />
Warren, S. 1211, 1215<br />
Witulski, B. 1223<br />
Yakura, T 1313<br />
Yamamoto, H. 1283<br />
Zhang, L. H. 1245<br />
Zhang, W. 1319<br />
Zhao, H. 1280<br />
Zumbrunn, C. 1295