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Asymmetric Synthesis of trans ‐β‐Lactams by a Kinugasa Reaction on Water
Author(s) -
Chen Zhenling,
Lin Lili,
Wang Min,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2013
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.201204373
Subject(s) - yield (engineering) , chemistry , environmentally friendly , enantioselective synthesis , reaction conditions , atom (system on chip) , combinatorial chemistry , catalysis , organic chemistry , materials science , computer science , ecology , metallurgy , biology , embedded system
The asymmetric Kinugasa reaction was performed on pure water for the first time without the need for any organic co‐solvents. In contrast to most asymmetric Kinugasa reactions, trans ‐β‐lactams were obtained as the major products in good yields, enantioselectivities, and diastereoselectivities (up to 90 % yield, 98 % ee , and >99:1 d.r.). This reaction is atom‐economical, environmentally friendly, and affords synthetically useful but challenging products.