A novel chiral sulfonium yilde: highly enantioselective synthesis of vinylcyclopropanes.
A newly designed chiral sulfonium allylide, generated in situ from the corresponding sulfonium salt in the presence of KOBu(t), reacted with alpha,beta-unsaturated esters, ketones, amides, and nitriles to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters, ketones, amides, and nitriles with outstanding diastereoselectivity and excellent enantioselectivity in good to high yields. A mechanistic rationale is proposed.
Ye
Song
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Huang
Zheng-Zheng
ZZ
Xia
Chun-An
CA
Tang
Yong
Y
Dai
Li-Xin
LX
D003521:Cyclopropanes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D003521:Cyclopropanes; D013452:Sulfonium Compounds; D014753:Vinyl Compounds