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N‐Heterocyclic‐Carbene‐Catalyzed Asymmetric Oxidative Hetero‐Diels–Alder Reactions with Simple Aliphatic Aldehydes
Author(s) -
Zhao Xiaodan,
Ruhl Kyle E.,
Rovis Tomislav
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206490
Subject(s) - carbene , deprotonation , chemistry , yield (engineering) , catalysis , enantioselective synthesis , organic chemistry , oxidative phosphorylation , medicinal chemistry , materials science , metallurgy , biochemistry , ion
An efficient enantioselective approach to form trans lactams and cis lactones in up to 98 % yield with greater than 99 % ee , and greater than 20:1 d.r. using simple aliphatic aldehydes has been developed. The process involves a new pathway to generate enolate intermediates from aliphatic aldehydes by oxidation and deprotonation. NHC=N‐heterocyclic carbene, Ts=4‐toluenesulfonyl.