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The Asymmetric Horner–Wadsworth–Emmons Reaction Mediated by An External Chiral Ligand
Author(s) -
Mizuno Masashi,
Fujii Kunihiko,
Tomioka Kiyoshi
Publication year - 1998
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/(sici)1521-3773(19980302)37:4<515::aid-anie515>3.0.co;2-q
Subject(s) - chemistry , enantiomer , ligand (biochemistry) , lithium (medication) , aryl , medicinal chemistry , stereochemistry , organic chemistry , psychology , receptor , biochemistry , alkyl , psychiatry
The astonishingly simple chiral ligand 1 was used in the first asymmetric variant of the Horner–Wadsworth–Emmons reaction. The products of olefination of 4‐substituted cyclohexanones with lithium phosphanates arise via the resulting hydroxyphosphonates, which are present in high enantiomeric excess (see scheme below). R=aryl, vinyl; R′=Me, t Bu, Ph.