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Stereoselective Synthesis of Highly Functionalized Nitrocyclopropanes through the Organocatalyic Michael‐Addition‐Initiated Cyclization of Bromonitromethane and β,γ‐Unsaturated α‐Ketoesters
Author(s) -
Yu Haijian,
Wang Qiaohui,
Wang Youming,
Song Haibing,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300778
Subject(s) - michael reaction , enantioselective synthesis , cyclopropanation , domino , intramolecular force , stereoselectivity , alkylation , chemistry , addition reaction , organic chemistry , catalysis
Abstract A highly diastereo‐ and enantioselective cyclopropanation of β,γ‐unsaturated α‐ketoesters with bromonitromethane has been successfully developed through a domino Michael‐addition/intramolecular‐alkylation strategy. Acceptable yields (up to 89 %) and enantioselectivities (up to 96 % ee ) have been obtained.