Highly diastereoselective formation of 1,2,3-trisubstituted cyclopropane derivatives.
A highly diastereoselective formation of cyclopropane derivatives was reported. When the chiral phenylvinyl epoxide reacted with lithiated 2-alkyl-1,3-dithiane or lithiated alkyl carbonanion in the presence of HMPA, cyclopropanes bearing stereochemistry at all three positions on the ring were readily obtained in high yields of 80-97% and high dr values of 68:32-99:1. This reaction was supposed to be a tandem conjugation addition-epoxide opening sequence. [reaction: see text]
Xie
Xingang
X
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 730000 Lanzhou, P. R. China.
Yue
Guoren
G
Tang
Shouchu
S
Huo
Xing
X
Liang
Qiren
Q
She
Xuegong
X
Pan
Xinfu
X