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Cationic‐Oxazaborolidine‐Catalyzed Enantioselective Diels–Alder Reaction of α,β‐Unsaturated Acetylenic Ketones
Author(s) -
Payette Joshua N.,
Yamamoto Hisashi
Publication year - 2009
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.200904339
Subject(s) - cationic polymerization , trimethylsilyl , adduct , enantioselective synthesis , catalysis , chemistry , yield (engineering) , diene , diels–alder reaction , bridged compounds , medicinal chemistry , organic chemistry , materials science , metallurgy , natural rubber
Yne also a good dienophile : The cationic oxazaborolidine 1 promoted the formation of Diels–Alder adducts between acetylenic ketones and both cyclic and acyclic dienes in excellent yield with 99 % ee (see scheme; Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl). Importantly, high levels of asymmetric induction were also observed with dienophiles that lacked the typical hydrogen‐bonding motif required for other oxazaborolidinium‐mediated reactions.