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Cationic Chiral Pd‐Catalyzed “Acetylenic” Diels–Alder Reaction: Computational Analysis of Reversal in Enantioselectivity
Author(s) -
Honda Kazuya,
Ohkura Shun,
Hayashi Yoshihiro,
Kawauchi Susumu,
Mikami Koichi
Publication year - 2018
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.201801035
Subject(s) - steric effects , cationic polymerization , selectivity , enantioselective synthesis , diels–alder reaction , chemistry , catalysis , organic chemistry
The highly enantioselective Diels–Alder reaction of acetylenic dienophiles is shown to be effectively catalyzed by cationic chiral palladium complexes. Not only the degree but also the sense of enantioselectivity critically depends on the steric demand of ligands. Computational analyses indicate that the steric demand does not affect the endo / exo ‐selectivity but the enantioface selectivity of dienes.