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Highly Diastereoselective Construction of Fused Carbocycles from Cyclopropane‐1,1‐dicarboxylates and Cyclic Enol Silyl Ethers: Scope, Mechanism, and Origin of Diastereoselectivity
Author(s) -
Qu JianPing,
Liang Yong,
Xu Hao,
Sun XiuLi,
Yu ZhiXiang,
Tang Yong
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103495
Subject(s) - cyclopropane , silylation , stereocenter , cyclopentane , enol , chemistry , cycloaddition , intermolecular force , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , molecule , ring (chemistry)
Cyclopropane rings true : By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through Cu II /bisoxazoline‐catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane‐1,1‐dicarboxylates and cyclic enol silyl ethers (see scheme).