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The Use of Vinyl Sulfonium Salts in the Stereocontrolled Asymmetric Synthesis of Epoxide‐ and Aziridine‐Fused Heterocycles: Application to the Synthesis of (−)‐Balanol
Author(s) -
Unthank Matthew G.,
Hussain Nigel,
Aggarwal Varinder K.
Publication year - 2006
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.200602782
Subject(s) - sulfonium , aziridine , epoxide , chemistry , organic chemistry , combinatorial chemistry , salt (chemistry) , catalysis , ring (chemistry)
Lift your ylides : An asymmetric, epoxy‐annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and ‐ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine‐annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts=toluene‐ p ‐sulfonyl, Tf=trifluoromethanesulfonyl).