synlett 17/2009 - Thieme Chemistry

SYNLETT
2715 Y. Zhang
Z. Lu
W. D. Wulff*
2740 F. Babudri
G. M. Farinola
F. Naso*
2749 M. Breuning*
M. Steiner
D. Hein
C. Hörl
P. Maier
Accounts and 2009
Rapid Communications in No. 17
Synthetic Organic Chemistry October II
Catalytic Asymmetric Aziridination with Catalysts Derived from VAPOL
and VANOL
Ph
Ph
R
OH
OH
(S)-VANOL
N CHPh2
Ph
Ph
O
+ OEt
N2
OH
OH
(S)-VAPOL
VANOL- or VAPOL-
CHPh2
B(OPh)3 catalyst N
R
CO 2Et
chiral aziridines
discovery optimization application
Organometallic Strategies for the Synthesis of Conjugated Oligomers
R
Ar
R
n
F
F
Ar
F
F
Ar
G
n
n
n
H
SAc
S
SAc S
H n
n
RO
OR
Thieme Chemistry Journal Awardees – Where Are They Now?
Bridgehead Lithiated 9-Oxabispidines
H
O
NMe
N
R 1 R 2
s-BuLi, Et2O –78 °C
Li
O
NMe
N
R 1 R 2
(+ regioisomer)
E-X,
–78 °C to r.t.
43–89%
E
O
OR
O
O
(+ regioisomer)
S
OR
NMe
n
N
R 1 R 2
–78 °C to r.t.
36–46%
Me
O
NMe
N
R1 R2 E = D, Me, TMS, Bz
(+ regioisomer)
H
S
H
n
Accounts
Letters

Letters
VI Table of Contents
2755 F. Hahn
U. Schepers*
2761 J. Tallineau
G. Bashiardes
J.-M. Coustard
F. Lecornué*
2765 C. Alp
U. Atmaca
M. Çelik
M. S. Gültekin*
2769 J. Clayden*
J. Senior
Thieme Chemistry Journal Awardees – Where are They Now?
A Convenient Route for Introduction of Lipophilic Side Chains in Polyamine
Backbones by Solid-Phase Synthesis
cargo
N
H
N N
H
side chain
N
Aloc
side chain
Aloc
N
H
N
solid-phase synthesis
o-Ns
N N
head group
n
A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to
the Total Synthesis of (±)-Laurokamurene B
Br
R 1
1) n-BuLi, THF, –78 °C
2) CeCl 3, THF, –78 °C
3)
R2 n
O
–78 °C to r.t.
4) DBU, MsCl or SOCl2
–30 °C to r.t.
10 examples, 17–93% yield
R 2
R 1
n
n = 1–4
(±)-laurokamurene B
One-Pot Synthesis of 1,2,3-Triols from Allylic Hydroperoxides and a
Catalytic Amount of OsO 4 in Aqueous Acetone
OOH OH
0.2 mmol% OsO4
H2O–acetone (1:9)
r.t., 30–94%
Synthesis of 2,2′,6-Trisubstituted and 2,2′,6,6′-Tetrasubstituted Diaryl
Sulfides and Diaryl Sulfones by Copper-Promoted Coupling and/or
Ortholithiation
+
Br
SH I
OH
OH
CuI, K 2CO 3
ethylene glycol
t-amyl alcohol
120 °C, 16 h
S
Br
76%

Table of Contents VII
2773 K. Bahrami*
M. M. Khodaei*
M. Soheilizad
2777 N. Assimomytis
Y. Sariyannis
G. Stavropoulos
P. G. Tsoungas*
G. Varvounis
P. Cordopatis
2783 V. P. Reddy
K. Swapna
A. V. Kumar
K. R. Rao*
2789 M.-A. Bazin
M. Jouanne
H. El-Kashef
S. Rault*
A Novel, Practical Synthesis of Sulfonyl Chlorides from Thiol and Disulfide
Derivatives
R SH
(i)
O
(ii)
R S Cl
O
RS SR
Reagents and conditions:
(i) H2O 2 (3 mmol), ZrCl 4 (1 mmol), MeCN, 25 °C;
(ii) H2O2 (2 mmol), ZrCl4 (1 mmol), MeCN, 25 °C
Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based
Mannich Bases
OCONR2 OH O
OH
R
NR2
2
R1 R2 R1 R2 R1 s-BuLi
LiAlH4 TMEDA
THF
–78 °C
THF
0 °C
to r.t.
R1 , R2 69–81% 65–79%
=HC C
H
C
H
CH, or H R = alkyl, cycloalkyl or heterocycloalkyl
Recyclable Nano Copper Oxide Catalyzed Stereoselective Synthesis of Vinyl
Sulfides under Ligand-Free Conditions
I
R
or +
R I
R'SH
R = R' = alkyl, aryl
CuO (1.5 mol%), DMSO (2.0 mL)
KOH (1.5 equiv), 80 °C
NR2
R
S
R'
or
R S R'
An Efficient Microwave-Promoted Route to (Z)-Stilbenes from
trans-Cinnamic Acids: Synthesis of Combretastatin A-4 and Analogues
R 1
R 1
CO2H
Br2, CHCl3, r.t., 2 h
60–95%
Br
R 1
B(OH)2
R
, Pd(PPh3)4
2
DME–H2O, base,
100 °C, MW, 15 min
21–86% (2 steps)
Br
Br
CO2H
Et3N, DMF,
140 °C, MW, 1 min
R1 R2
Letters

Letters
VIII Table of Contents
2795 C. Praveen
S. Jegatheesan
P. T. Perumal*
2801 M. G. Gonçalves-Martin
A. Saxer
P. Renaud*
2803 S. Hanessian*
X. Wang
2809 H.-G. Lee
M.-J. Kim
S.-E. Park
J.-J. Kim
B. R. Kim
S.-G. Lee
Y.-J. Yoon*
Gold(III) Chloride Catalyzed Intermolecular Dimerization of
2-Ethynylanilines: Synthesis of Substituted Quinolines
R
NH2
+
R
NH2
5 mol% AuCl3, 10 mol% AgOTf
MeCN, N 2, reflux
A Practical Synthesis of (S)-Cyclopent-2-enol
OH
S
O
SiMe 3
Applications of the N-tert-Butylsulfonyl (Bus) Protecting Group in Amino
Acid and Peptide Chemistry
R
H2N CO2Me
R
BusHN CO 2Me
R = Me, i-Pr, CH 2CO 2Me, Bn, i-Bu, etc.
R
R
H 2N CO 2Me
Phenyl 4,5-Dichloro-6-Oxopyridazine-1(6H)-Carboxylate as Carbonyl
Source: Facile and Selective Synthesis of Carbamates and Ureas under Mild
Conditions
R 1 R 2 NH
alkyl or aryl
amines
Cl
Cl
N N
O
C
O O
THF
– 4,5-dichloropyridazin-3(2H)-one
O
2 R 1 RN O
R
N
1
O
R2 N
O
Me
N
2 R 1 RN NR 3 R 4
carbamates unsymmetric ureas
R 1
R 2
symmetric ureas
NH2
R

Table of Contents IX
2815 R. Jiang
X.-P. Xu*
T. Chen
H.-Y. Li
G. Chen
S.-J. Ji*
2821 S.-J. Yan
Y.-F. Niu
R. Huang
J. Lin*
2825 N. Yasmin
J. K. Ray*
2828 J. S. Yadav*
T. S. Rao
K. Ravindar
B. V. S. Reddy
Bismuth(III)-Promoted C3-Ferrocenyl Alkylation of Indoles
OH
R1 5 mol% Bi(NO3) 3⋅5H2O + R
N
H
2
Fe R2 H
MeCN, r.t.
R 1 = H, Me, Ph R 2 = H, Me, Ph, Br, BnO, NO 2
R 1
N
H
62–96%
Synthesis of Bicyclic Pyridones via Cyclocondensation of Heterocyclic
Ketene Aminals with b-Ketoester Enol Tosylates
Z
n
N
H
EWG
H
TsO
+ R
O
OEt
(E)
dioxane
Et3N reflux
Z
n
N
EWG
R
O
n = 1–2; Z = NH, O; R = CF3, Me
EWG = NO2, COMe, COOEt, COAr
25 examples
80–95% yield
A Simple One-Pot Synthesis of 2-Aryl-5-alkyl-Substituted Oxazoles by
Cs 2CO 3-Mediated Reactions of Aromatic Primary Amides with 2,3-Dibromopropene
O Br
R NH2
+
R = aryl, cinnamyl
Br
Cs2CO 3
DMSO, 110 °C, 2–3 h
Total Synthesis of (+)-Aspicilin from D-Mannitol
D-mannitol
OBn OTES
OBn
CHO
R
O
N
OH
OH
OH
(+)-aspicilin
O
O
Fe
Letters

Letters
X Table of Contents
2831 Y. Yue
H. Yamamoto
M. Yamane*
2836 J. Clayden*
J. Clayton
R. A. Harvey
O. Karlubíková
2839 R. K. Gessner
K. Chibale*
2844 I. González
A. Pla-Quintana
A. Roglans*
Rhodium-Catalyzed Homocoupling of (1-Acyloxyvinyl)silanes: Synthesis of
1,3-Diene-2,3-diyl Diesters and Their Derivatives
OCOR
SiMe3
2
R1 5 mol%
[RhCl(CO)2]2
Cl3CCOCCl3 toluene, 80 °C
OCOR2 R1 OCOR2 R1 R1 = aryl, alkyl R2 = Me, Ph, OEt, etc. 18–92%
R1 R1 MeO OMe
O
R1 = Ph(CH2) 2 R2 K2CO3 MeOH
= Ph 87%
A One-Pot Synthesis of 2-Aryl-4,5-anti-diphenyloxazolines
O
Cl
R
Ph Ph
(S) (R)
HO
NH2
Et 3N (4 equiv),
CH 2Cl 2, 0–25 °C
HO
O
Ph
NH
R
Ph
MeSO 2Cl,
0–25 °C
Ph
O
N
R
Ph
(R) (R)
13 examples
20–90% yield
A New and Simple Synthesis of Sulfonyl Ureas from Sulfonamides and
N-Alkyl-1,2,4-dithiazolidine-3,5-diones
S
S
O
O
NH
Br R 1
NaHCO3, MeCN
20 °C, 16 h
S
S
O
O
N
R 1
O O
H2N S R 2
Ph3P, K2CO3
PhMe, reflux, 24 h
O O
R
S
N
H
2
Rhodium N-Heterocyclic Carbene Complexes as Effective Catalysts for
[2+2+2]-Cycloaddition Reactions
R
N
Cl
N R
Rh
R = i-Pr, Mes
O
N
H
R 1

Table of Contents XI
2849 J.-Y. Wach
K. Gademann*
2852 L. Ackermann*
H. K. Potukuchi
2857 C. Macleod
P. A. Tuthill
R. E. Dolle*
2862 Y. Wang
J. Wu
W.-M. Dai*
Enantioselective Synthesis of the Sporolide Quinone Acid Fragment
OH
R 2
O O
O
R
O
O
1
Me
OH
OH
O
OH
HO
sporolide A: R1 = Cl, R2 = H
sporolide B: R1 = H, R2 MeO
= Cl
HO
O
OMe
O
O
sporolide quinone acid
Palladium-Catalyzed Cross-Coupling Reactions of 2-Pyridylborates with
Air-Stable HASPO Preligands
Pd2(dba)3 (1.0 mol%)
Ar Ar
Me
Me
O
O
O O
P
H
O
Br
Ar Ar
X X
R
(4.0 mol%)
K3PO4, 1,4-dioxane
110 °C, 20 h
2
R
N
+
B(Oi-Pr) 3Li
Ar = 4-FC6H4 1 R1 X = CH, N
OH
Me
N
X
X
R2 N-Alkylation–Intramolecular Michael Addition: New Reaction Manifold for
High Throughput Annulation of Amines
RNH2 SPAn
reagent n
N
R
X
Y
N
R
O
O
n
N
R
N Me
Stereoselectivity of Intramolecular Diels–Alder Reaction of Hydroxamate-
Tethered 1,3,9-Decatrienes under Thermal and Microwave Heating
MW
O
MeCN, 180 °C O
Bn
N
10
R
30 min,
Bn
N
10
R
dr = 60:40 to
90:10
O
5 3 1
Me
O
5
3 1
dr = 90:10 to 100:0
R = H, Me, Ph
Me
Bn
N
O
H
R
Me Bn
N
O
H
R
Me Bn
N
O
H
R
Bn
N
O
H
R
O
+
O
O
+
O
H
(major)
H
(minor)
H
Me
(major)
H
Me
(minor)
O
Letters

Letters
Spotlights
XII Table of Contents
2867 K.-L. Li
C.-C. Guo*
Q.-Y. Chen*
2872 D. Enders*
H. Saeidian
Z. Mirjafary
D. Iffland
G. Raabe
J. Runsink
2875 F. Hamon
B. Violeau
F. Turpin
M. Bellot
L. Bouteiller
F. Djedaini-Pilard
C. Len*
2880 Compiled by
U. D. Patil
Efficient One-Pot Regioselective Synthesis of 2,3-Dibromo-5,10,15,20-tetraarylporphyrins
from 5,10,15,20-Tetraarylchlorins
Ar
NH N
N
Ar
HN
Ar
Ar
easily available,
60–85% yield from H2TArP
(1) NBS, CHCl3,
N2, reflux, 4 h
(2) DDQ, CHCl3,
air, reflux, 1 h
Ar
NH N
N
Ar
HN
Ar
95–96%
Diastereo- and Enantioselective Synthesis of a,b-Disubstituted
g-Bisalkoxycarbonyl Sulfonates
O
O
R1 =
S
O O
OR1 O
O
O
MeO 2C
CO2Me
EWG 1
R2 EWG2 62–79%
SO 3i-Pr
de, ee = >98%
Me
EWG 2
48%
R 1 = i-Pr
R 2 = p-Tol
R
S
2
EWG1 O O
OR1 ds = 69–96%
Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs
Bestmann–Ohira Reagent:
A Versatile Reagent in Organic Synthesis
Br
Br
Ar

Table of Contents XIII
2882 Compiled by
H. Ghosh*
2884 Erratum
XV Forthcoming Articles
1,3-Disubstituted Thioureas: Versatile Building Blocks for the Construction
of Heterocycles
Spotlights
Addenda and Errata

XIV Table of Contents
Author Index
Ackermann, L. 2852
Alp, C. 2765
Assimomytis, N. 2777
Atmaca, U. 2765
Babudri, F. 2740
Bahrami, K. 2773
Bashiardes, G. 2761
Bazin, M.-A. 2789
Bellot, M. 2875
Bouteiller, L. 2875
Breuning, M. 2749
Çelik, M. 2765
Chen, G. 2815
Chen, Q.-Y. 2867
Chen, T. 2815
Chibale, C. 2839
Clayden, J. 2769, 2836
Clayton, J. 2836
Cordopatis, P. 2777
Coustard, J.-M. 2761
Dai, W.-M. 2862
Djedaini-Pilard, F. 2875
Dolle, R. E. 2857
El-Kashef, H. 2789
Enders, D. 2872
Farinola, G. M. 2740
Gademann, K. 2849
Gessner, R. K. 2839
Ghosh, H. 2882
Gonçalves-Martin, M. G. 2801
González, I. 2844
Gültekin, M. S. 2765
Guo, C.-C. 2867
Hahn, F. 2755
Hamon, F. 2875
Hanessian, S. 2803
Harvey, R. A. 2836
Hein, D. 2749
Hörl, C. 2749
Huang, R. 2821
Iffland, D. 2872
Jegatheesan, S. 2795
Ji, S.-J. 2815
Jiang, R. 2815
Jouanne, M. 2789
Karlubíková, O. 2836
Khodaei, M. M. 2773
Kim, B. R. 2809
Kim, J.-J. 2809
Kim, M.-J. 2809
Kumar, A. V. 2783
Lecornué, F. 2761
Lee, H.-G. 2809
Lee, S.-G. 2809
Len, C. 2875
Li, H.-Y. 2815
Li, K.-L. 2867
Lin, J. 2821
Lu, Z. 2715
Macleod, C. 2857
Maier, P. 2749
Mirjafary, Z. 2872
Naso, F. 2740
Niu, Y.-F. 2821
Park, S.-E. 2809
Patil, U. D. 2839
Perumal, P. T. 2795
Pla-Quintana, A. 2844
Potukuchi, H. K. 2852
Praveen, C. 2795
Raabe, G. 2872
Rao, K. R. 2783
Rao, T. S. 2828
Rault, S. 2789
Ravindar, K. 2828
Ray, J. K. 2825
Reddy, B. V. S. 2828
Reddy, V. P. 2783
Renaud, P. 2801
Roglans, A. 2844
Runsink, J. 2872
Saeidian, H. 2872
Sariyannis, Y. 2777
Saxer, A. 2801
Schepers, U. 2755
Senior, J. 2769
Soheili, M. 2773
Stavropoulos, G. 2777
Steiner, M. 2749
Swapna, K. 2783
Tallineau, J. 2761
Tsoungas, P. G. 2777
Turpin, F. 2875
Tuthill, P. A. 2857
Varvounis, G. 2777
Violeau, B. 2875
Wach, J.-Y. 2849
Wang, X. 2803
Wang, Y. 2862
Wu, J. 2862
Wulff, W. D. 2715
Xu, X.-P. 2815
Yadav, J. S. 2828
Yamamoto, H. 2831
Yamane, M. 2831
Yan, S.-J. 2821
Yasmin, N. 2825
Yoon, Y.-J. 2809
Yue, Y. 2831
Zhang, Y. 2715