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Enantioselective Bromolactonization Using an S ‐Alkyl Thiocarbamate Catalyst
Author(s) -
Jiang Xiaojian,
Tan Chong Kiat,
Zhou Ling,
Yeung YingYeung
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.201202079
Subject(s) - thiocarbamate , thiocarbamates , alkyl , yield (engineering) , enantioselective synthesis , catalysis , chemistry , organic chemistry , materials science , metallurgy
The apple never falls far from the tree : S ‐alkyl thiocarbamate 1 (see scheme, NBP= N ‐bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman–Kwart rearrangement of the corresponding O ‐alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ‐lactones in excellent yield and enantioselectivity.