. Author manuscript; available in PMC: 2011 Apr 14.

Published in final edited form as: Tetrahedron Lett. 2010 Apr 14;51(15):2032–2035. doi: 10.1016/j.tetlet.2010.02.050

Table 1.

Intermolecular Michael additions of carbon nucleophiles to nitrosoalkenes

entry	ester derivative	nitrosoalkene precursor	product	yield
a				95%^a
b				84%
c				69%
d				57%^b,^c
e				71%^c
f				95%^c
g				79%^c
h				85%^d,^e
i				72%
j				73%
k				82%^c
l				55%^c,^d
m				64%^d,^e
n				74%
o				69%^d
p				63%
q				88%
r				71%
s				75%
t				51%^f
u				69%
v				68%^d,^g
w				75%^c,^d
x				67%^d

Use of LiHMDS and NaHMDS gave yields of 91% and 94%, respectively.

No desired product was formed when using LiHMDS or NaHMDS.

An accurate stereochemical assignment could not be made since the products exist as a complex mixture of E/Z-isomers and/or diastereomers which were not separable by column chromatography.

2 eq of KHMDS and 2 eq of ester derivative were used.

The deprotonation step was performed at 0 °C to prevent freezing of the reaction mixture.

Use of LiHMDS and NaHMDS gave 34% and 51%, respectively.

E:Z ratio could not be determined.