synlett 07/2007 - Thieme Chemistry

Letters
VI Table of Contents
1031 A. Arcadi*
G. Bianchi
A. Inesi
F. Marinelli
L. Rossi*
1037 H. Habib-Zahmani
J. Viala*
S. Hacini
J. Rodriguez*
1043 R. Hodgson
A. Kennedy
A. Nelson*
A. Perry*
1047 S. Perrone
A. Metzger
P. Knochel*
Sequential Alkylation/Heterocyclization of b-(2-Aminophenyl)-a,b-ynones
Promoted by Electrogenerated Carbanions: A New Approach to
Functionalized 4-Alkylquinolines
R-H
electrolysis
R 2
R 3
Synthesis of Functionalized Spiroheterocycles by Sequential
Multicomponent Reaction/Metal-Catalyzed Carbocylizations from
Simple b-Ketoesters and Amides
X
O O
Br
( )n
z
+
Y R
+
ArCHO
DBU
THF–MeOH
Ar
X
O
( ) n
O
z
Y
NH 2
O
R 1
R 2
RCM
Ar
YR = N(allyl)Me
= O(allyl)
Heck
R YR = N(allyl)Me
Buchwald
YR = NHPh
Ar
R 3
X
O
Ar
X
O
( )n
R
N
O
X
O
O
Y
R 1
N
O
N Ph
Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of a-Furylsulfonamides
and N→O Sulfonyl Transfer
O
R
NHTs
NBS
or
MCPBA
O
HO N R
Ts
R = alkyl, aryl or heteroaryl
Chiral Allylic Cyanohydrins as Versatile Substrates for Diastereoselective
Copper(I)-mediated S N2¢ Allylic Substitutions
2,6-F 2C 6H 3
O
O
CN
R2Zn (2.4 equiv)
CuCN·2LiCl (1.2 equiv)
n Me
THF–NMP (2:1)
–30 °C
n
n = 1, 96% ee
n = 0, 90% ee
AlCl3
CN
R
Me
up to 96% ee
40–91% yield
N
OTs
R