title: A novel chiral sulfonium yilde: highly enantioselective synthesis of vinylcyclopropanes.
abstract: 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.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: Song
authors.initials: S
authors.lastname: Ye
authors.forename: Zheng-Zheng
authors.initials: ZZ
authors.lastname: Huang
authors.forename: Chun-An
authors.initials: CA
authors.lastname: Xia
authors.forename: Yong
authors.initials: Y
authors.lastname: Tang
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Dai
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: D003521:Cyclopropanes; D013452:Sulfonium Compounds; D014753:Vinyl Compounds