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<strong>SYNTHESIS</strong><br />
2595<br />
Intermolecular C–H Insertions of<br />
Donor/Acceptor-Substituted Rhodium Carbenoids:<br />
A Practical Solution for Catalytic Enantioselective<br />
C–H Activation<br />
H. M. L. Davies,* Ø. Loe<br />
2609<br />
The First Synthesis of 1,1-Dinitrocyclopropane<br />
E. M. Budynina, E. B. Averina, O. A. Ivanova, N. V. Yashin,<br />
T. S. Kuznetsova,* N. S. Zefirov<br />
2611<br />
Improved Synthesis of<br />
2,3-Dibromo-1-(phenylsulfonyl)-1-propene (DBP)<br />
A. VanZanten, K. Mullaugh, R. Harrington, A. Kiefer, D. Carlson,<br />
D. Mastarone, C. Lipchik, S. S. Murphree*<br />
2614<br />
A Concise Synthesis of 2,4-Disubstituted Pyridines:<br />
A Convenient Synthesis of 2-Bromo-4-iodopyridine<br />
via Halogen Dance and Its Successive One-Pot<br />
Disubstitutions<br />
X.-F. Duan,* X.-H. Li, F.-Y. Li, C.-H. Huang<br />
Journal of 2004<br />
Synthetic Organic No. 16<br />
Chemistry November<br />
R 1<br />
R2 R3 N2 + H<br />
2617<br />
The Huisgen Reaction of Azomethine Ylide to Isatins:<br />
A Facile Synthesis of Spiro-oxindoles<br />
Me<br />
V. Nair,* S. Mathai, A. Augustine, S. Viji, K. V. Radhakrishnan N<br />
CO 2Me<br />
EDG<br />
Rh2(S-DOSP)4<br />
R 1<br />
R2 R3 H<br />
2Me CO<br />
EDG<br />
= aryl or vinyl Regioselectivity<br />
EDG<br />
Diastereoselectivity<br />
benzene<br />
3 + CH2N2 2) HC(NO<br />
Me<br />
one<br />
0.5 h<br />
NO2<br />
NO 2<br />
SO2Ph pot Cl<br />
Br N Br<br />
N<br />
ArMgBr/[Pd]<br />
1<br />
Me<br />
Si<br />
LDA / I2<br />
Ar'MgBr/[Pd]<br />
2<br />
PySnBu3/[Pd] or<br />
Ph<br />
+<br />
OMe<br />
+<br />
O<br />
23%<br />
62%<br />
I<br />
N<br />
O<br />
Me<br />
LDA / H +<br />
Ar<br />
one<br />
pot<br />
N Ar'(Py)<br />
TFA (cat)<br />
I<br />
Enantioselectivity<br />
N<br />
Br<br />
SO2Ph<br />
N Br<br />
O<br />
O<br />
r.t., 3 h N<br />
CH2Cl2,<br />
NO 2<br />
Me<br />
(82%)<br />
N<br />
O<br />
O<br />
Br<br />
Review<br />
Short Papers
Papers<br />
VI Table of Contents<br />
2620<br />
Indium(III) Halide Mediated SN2¢ Reactions of Substituted<br />
Allenols: Synthesis of 2-Halo-1,3-dienes<br />
Y. S. Cho,* B. K. Jun, A. N. Pae, J. H. Cha, H. Y. Koh,<br />
M. H. Chang, S.-Y. Han<br />
2625<br />
Efficient Synthesis of 4-(3-Fluoro-5-{[4-(2-methyl-1Himidazol-1-yl)benzyl]-oxy}phenyl)tetrahydro-2Hpyran-4-carboxamide,<br />
a Novel 5-Lipoxygenase<br />
Inhibitor<br />
T. Mano,* R. W. Stevens, K. Nakao, Y. Okumura, K. Kawamura,<br />
A. Ando, Y. Matsuoka<br />
2629<br />
Efficient Activation of Zinc: Application of the Blaise<br />
Reaction to an Expedient Synthesis of a Statin<br />
Intermediate<br />
H. Shin,* B. S. Choi, K. K. Lee, H.-w. Choi, J. H. Chang,<br />
K. W. Lee, D. H. Nam, N.-S. Kim*<br />
2633<br />
Stereoselective Reduction of b-Hydroxy a-Ketoesters:<br />
A Concise Synthesis of anti-a,b-Dihydroxy Esters<br />
R 1<br />
OH<br />
R 2<br />
InX 3<br />
benzene, 3 °C ~ r.t.<br />
(X = Cl, Br)<br />
O<br />
1) N2CHCO2Et, DBU<br />
2) Dimethyldioxirane<br />
Acetone, –35 °C<br />
M. Liao, W. Yao, J. Wang* R H 3) NaBH4, CH2Cl2<br />
–63 °C to r.t.<br />
Overall yields: 36–78%<br />
dr >95:5 (R = Ar)<br />
dr 85:15 – 93:7 (R = Alkyl)<br />
2637<br />
A Tandem Nucleophilic Addition, Defluorination and<br />
Destannylation. Stereospecific Synthesis of<br />
Trifluoromethylated Alkyl and Aryl Vinyl Ethers<br />
Y. Shen,* G. Wang<br />
2641<br />
A Convenient Halogenation of a,b-Unsaturated<br />
Carbonyl Compounds with OXONE ® and Hydrohalic<br />
Acid (HBr, HCl)<br />
K.-M. Kim,* I.-H. Park<br />
F3C<br />
Ar<br />
1<br />
= Me or Et<br />
R<br />
= Ar R'<br />
R 1<br />
O<br />
R 2<br />
SnBu 3<br />
F<br />
OXONE<br />
R 1<br />
OH<br />
R 2<br />
O<br />
X<br />
R OEt<br />
OH<br />
RONa/ROH<br />
R'OH/K2CO3<br />
DMF<br />
Et3N<br />
R1 X<br />
N HX CH2Cl2 2<br />
CH 2Cl 2<br />
R1 H, alkyl, aryl, alkoxy<br />
=<br />
R2 alkyl, aryl, aryloxy<br />
=<br />
O<br />
R 2<br />
X<br />
20–99%<br />
+<br />
F3C<br />
Ar<br />
R 1<br />
F 3C<br />
Ar<br />
R 1<br />
O<br />
R 2<br />
R 2<br />
2<br />
3<br />
X<br />
X<br />
= Cl: 20–82%<br />
X<br />
= Br: 37–99%<br />
X<br />
H<br />
OR<br />
H<br />
OR'
Table of Contents VII<br />
2645<br />
Highly Diastereoselective Peptide Chain Extensions<br />
of Unprotected Amino Acids with<br />
N-(Z-a-Aminoacyl)benzotriazoles<br />
A. R. Katritzky,* K. Suzuki, S. K. Singh<br />
2653<br />
N-Acylation of 5-Substituted Indoles with Carboxylic<br />
Acids via DCC Coupling<br />
J. B. Bremner,* S. Samosorn, J. I. Ambrus<br />
2659<br />
2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in<br />
the Synthesis of New Condensed Pyrimidines<br />
Y. M. Volovenko, E. V. Blyumin,* T. A. Volovnenko,<br />
T. V. Shokol, O. V. Shishkin<br />
2665<br />
Synthesis of New Polycyclic b-Lactams via One-Pot<br />
Enyne Metathesis and Diels–Alder Reactions<br />
N. Desroy, F. Robert-Peillard, J. Toueg, C. Hénaut, R. Duboc,<br />
M.-N. Rager, M. Savignac,* J.-P. Genêt*<br />
2673<br />
Environmentally Benign Preparation of<br />
Heteroaromatics from Ketones or Alcohols, with<br />
Macroporous Polystyrenesulfonic Acid and<br />
(Diacetoxyiodo)benzene, Followed by Thioamide,<br />
Amidine, and 2-Aminopyridine<br />
M. Ueno, H. Togo*<br />
2678<br />
New Synthetic Approach for the Preparation of<br />
Imidazole N3-Oxide H. Cerecetto,* A. Gerpe, M. González,* Y. Fernández Sainz,<br />
O. E. Piro, E. E. Castellano<br />
Z<br />
R<br />
R 1<br />
O<br />
NH Bt<br />
O<br />
OTBS<br />
N<br />
+<br />
N<br />
H<br />
n<br />
n = 1, 2<br />
+<br />
R 2<br />
H2N<br />
O<br />
OH<br />
COOH<br />
R 2<br />
R 1<br />
Et3N<br />
CH 3CN/H2O<br />
R<br />
DCC, DMAP<br />
2Cl2, r.t. CH<br />
h 2–72<br />
one-pot<br />
O<br />
O<br />
OTBS<br />
N<br />
Z<br />
N<br />
R 1<br />
NH<br />
n<br />
R 1<br />
O<br />
HN<br />
X<br />
X<br />
HO<br />
R 2<br />
R 2<br />
O<br />
Papers
Papers<br />
VIII Table of Contents<br />
2685<br />
The Synthesis of Tetrahydroquinolines Related to<br />
Virantmycin<br />
C. L. Francis, N. M. Williamson, A. D. Ward*<br />
2692<br />
Metal Triflate-Catalyzed One-Pot Synthesis of<br />
a-Aminophosphonates from Carbonyl Compounds<br />
in the Absence of Solvent<br />
H. Firouzabadi,* N. Iranpoor,* S. Sobhani<br />
2697<br />
Reactions of 1,4-Benzodiazepinic N-Nitrosoamidines<br />
with Tosylmethyl Isocyanide: A Novel Synthesis of<br />
Midazolam<br />
C. del Pozo,* A. Macías, E. Alonso, J. González*<br />
2704<br />
Chiral Carbanions, Part 4: Borylation of<br />
(Trimethylsilyl)methyl N,N-Dialkylcarbamates –<br />
Diastereoselectivity and Structural Studies<br />
B. P. Simov, A. Rohn, L. Brecker, G. Giester, F. Hammerschmidt*<br />
2711<br />
Rapid and Efficient Protocol for the Synthesis of<br />
4-Chlorotetrahydropyrans Using Niobium(V)<br />
Chloride<br />
J. S. Yadav,* B. V. S. Reddy, M. K. Gupta, S. K. Biswas<br />
2716<br />
Synthesis of Oligopyridinic Scaffolds from Amido<br />
Substituted Phenyl Rings for Extended Hydrogen<br />
Bonding<br />
G. Pickaert, R. Ziessel*<br />
Me<br />
OH<br />
O2N<br />
O OH<br />
O OEt<br />
OH<br />
NO 2<br />
H<br />
N<br />
H2N<br />
H2n+1CnO<br />
OMe<br />
Bu<br />
O OEt<br />
+<br />
Cl O<br />
NH2<br />
OCnH2n+1<br />
Me<br />
H2n+1CnO<br />
H2n+1CnO<br />
O<br />
O<br />
N N<br />
H H<br />
O<br />
H<br />
N<br />
N<br />
N<br />
n = 8, 12, 16<br />
N<br />
N<br />
OMe<br />
Bu<br />
Cl<br />
OCnH2n+1<br />
OCnH2n+1<br />
N<br />
Ph<br />
O N<br />
N
Table of Contents IX<br />
2727<br />
Tri(ethylene Glycol)- and Poly(ethylene Glycol) Ether<br />
End-Grafted Carbosiloxane and Carbosilane<br />
Dendrimers: Synthesis and Reaction Behavior<br />
R. Buschbeck, S. Mecklenburg, B. Lühmann, V. K. Gupta,<br />
H. Lang*<br />
2736<br />
Silica-Assisted Reactions of Pyrroles with<br />
1-Acyl-2-bromoacetylenes<br />
Z. V. Stepanova, L. N. Sobenina,* A. I. Mikhaleva, I. A. Ushakov,<br />
N. N. Chipanina, V. N. Elokhina, V. K. Voronov, B. A. Trofimov<br />
2743<br />
Synthesis and Properties of N-Arylcarbazolophane–<br />
Paracyclophane Combined with Carbazoles<br />
Y. Nakamura, T. Yamazaki, Y. Kakinoya, H. Shimizu,<br />
J. Nishimura*<br />
2747<br />
Efficient Syntheses of Novel Naphthaleno- and<br />
Anthraceno-Octafluoro[2.2]paracyclophanes<br />
Y. Zhai, I. Ghiviriga, M. A. Battiste, W. R. Dolbier Jr.*<br />
2751<br />
Cyclophanes. Part LII: Ethynyl[2.2]paracyclophanes –<br />
New Building Blocks for Molecular Scaffolding<br />
L. Bondarenko, I. Dix, H. Hinrichs, H. Hopf*<br />
2760<br />
Cyanoacetylation of Indoles, Pyrroles and Aromatic<br />
Amines with the Combination Cyanoacetic Acid and<br />
Acetic Anhydride<br />
J. Slätt, I. Romero, J. Bergman*<br />
HOH2C<br />
HOH 2C<br />
F2C CF2<br />
N O (CH 2) 3 O N<br />
CF2<br />
F2C CF 2<br />
CF2<br />
F2C CF 2<br />
CF2<br />
CH2OH<br />
H +<br />
CH 2OH<br />
O (CH2)3 O<br />
F2C<br />
F2C<br />
F2C<br />
6 7 8<br />
5<br />
N<br />
N<br />
F2C CF 2<br />
F2C<br />
CF2<br />
O<br />
O<br />
Papers<br />
Special Topics<br />
PSP
X Table of Contents<br />
Book Review<br />
Esterification Methods, Reactions and Applications 2766<br />
By J. Otera<br />
Reviewed by Nathalie Batoux<br />
Forthcoming Articles XIII<br />
Author Index<br />
Alonso, E. 2697<br />
Ambrus, J. I. 2653<br />
Ando, A. 2625<br />
Augustine, A. 2617<br />
Averina, E. B. 2609<br />
Battiste, M. A. 2747<br />
Bergman, J. 2760<br />
Biswas, S. K. 2711<br />
Blyumin, E. V. 2659<br />
Bondarenko, L. 2751<br />
Brecker, L. 2704<br />
Bremner, J. B. 2653<br />
Budynina, E. M. 2609<br />
Buschbeck, R. 2727<br />
Carlson, D. 2611<br />
Castellano, E. E. 2678<br />
Cerecetto, H. 2678<br />
Cha, J. H. 2620<br />
Chang, J. H. 2629<br />
Chang, M. H. 2620<br />
Chipanina, N. N. 2736<br />
Cho, Y. S. 2620<br />
Choi, B. S. 2629<br />
Choi, H.-w. 2629<br />
Davies, H. M. L. 2595<br />
del Pozo, C. 2697<br />
Desroy, N. 2665<br />
Dix, I. 2751<br />
Dolbier, W. R. Jr. 2747<br />
Duan, X.-F. 2614<br />
Duboc, R. 2665<br />
Elokhina, V. N. 2736<br />
Fernández Sainz, Y. 2678<br />
Firouzabadi, H. 2692<br />
Francis, C. L. 2685<br />
Genêt, J.-P. 2665<br />
Gerpe, A. 2678<br />
Ghiviriga, I. 2747<br />
Giester, G. 2704<br />
González, J. 2697<br />
González, M. 2678<br />
Gupta, M. K. 2711<br />
Gupta, V. K. 2727<br />
Hammerschmidt, F. 2704<br />
Han, S.-Y. 2620<br />
Harrington, R. 2611<br />
Hénaut, C. 2665<br />
Hinrichs, H. 2751<br />
Hopf, H. 2751<br />
Huang, C.-H. 2614<br />
Iranpoor, N. 2692<br />
Ivanova, O. A. 2609<br />
Jun, B. K. 2620<br />
Kakinoya, Y. 2743<br />
Katritzky, A. R. 2645<br />
Kawamura, K. 2625<br />
Kiefer, A. 2611<br />
Kim, K.-M. 2641<br />
Kim, N.-S. 2629<br />
Koh, H. Y. 2620<br />
Kuznetsova, T. S. 2609<br />
Lang, H. 2727<br />
Lee, K. K. 2629<br />
Lee, K. W. 2629<br />
Li, F.-Y. 2614<br />
Li, X.-H. 2614<br />
Liao, M. 2633<br />
Lipchik, C. 2611<br />
Loe, Ø. 2595<br />
Lühmann, B. 2727<br />
Macías, A. 2697<br />
Mano, T. 2625<br />
Mastarone, D. 2611<br />
Mathai, S. 2617<br />
Matsuoka, Y. 2625<br />
Mecklenburg, S. 2727<br />
Mikhaleva, A. I. 2736<br />
Mullaugh, K. 2611<br />
Murphree, S. S. 2611<br />
Nair, V. 2617<br />
Nakamura, Y. 2743<br />
Nakao, K. 2625<br />
Nam, D. H. 2629<br />
Nishimura, J. 2743<br />
Okumura, Y. 2625<br />
Pae, A. N. 2620<br />
Park, I.-H. 2641<br />
Pickaert, G. 2716<br />
Piro, O. E. 2678<br />
Radhakrishnan, K. V. 2617<br />
Rager, M.-N. 2665<br />
Reddy, B. V. S. 2711<br />
Robert-Peillard, F. 2665<br />
Rohn, A. 2704<br />
Romero, I. 2760<br />
Samosorn, S. 2653<br />
Savignac, M. 2665<br />
Shen, Y. 2637<br />
Shimizu, H. 2743<br />
Shin, H. 2629<br />
Shishkin, O. V. 2659<br />
Shokol, T. V. 2659<br />
Simov, B. P. 2704<br />
Singh, S. K. 2645<br />
Slätt, J. 2760<br />
Sobenina, L. N. 2736<br />
Sobhani, S. 2692<br />
Stepanova, Z. V. 2736<br />
Stevens, R. W. 2625<br />
Suzuki, K. 2645<br />
Togo, H. 2673<br />
Toueg, J. 2665<br />
Trofimov, B. A. 2736<br />
Ueno, M. 2673<br />
Ushakov, I. A. 2736<br />
VanZanten, A. 2611<br />
Viji, S. 2617<br />
Volovenko, Y. M. 2659<br />
Volovnenko, T. A. 2659<br />
Voronov, V. K. 2736<br />
Wang, G. 2637<br />
Wang, J. 2633<br />
Ward, A. D. 2685<br />
Williamson, N. M. 2685<br />
Yadav, J. S. 2711<br />
Yamazaki, T. 2743<br />
Yao, W. 2633<br />
Yashin, N. V. 2609<br />
Zefirov, N. S. 2609<br />
Zhai, Y. 2747<br />
Ziessel, R. 2716
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