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Selectivities in Chiral Lewis Acid Catalyzed Diels–Alder Reactions of Acetylenic Ketones: Explanation for Differences of Selectivities between Acylic and Cyclic Dienes
Author(s) -
Payette Joshua N.,
Akakura Matsujiro,
Yamamoto Hisashi
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000687
Subject(s) - cationic polymerization , chemistry , lewis acids and bases , catalysis , organic chemistry , diels–alder reaction , medicinal chemistry , computational chemistry
Huey Lewis (acid) and the News : Crystallographic and computational studies on the cationic‐oxazaborolidine‐catalyzed Diels–Alder reaction of acetylenic ketones indicated that the reaction proceeds through a favored syn, exo transition state. These results provide a basis for understanding why acyclic dienes give higher enantioselectivities than cyclic dienes.