Premium
Organocatalytic Asymmetric Sulfa‐Michael Addition to α,β‐Unsaturated Ketones
Author(s) -
Ricci Paolo,
Carlone Armando,
Bartoli Giuseppe,
Bosco Marcella,
Sambri Letizia,
Melchiorre Paolo
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700382
Subject(s) - chemistry , iminium , enantioselective synthesis , organocatalysis , michael reaction , nucleophile , reactivity (psychology) , amine gas treating , catalysis , organic chemistry , salt (chemistry) , selectivity , sulfur , medicinal chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
Abstract The highly enantioselective organocatalytic sulfa‐Michael addition to α,β‐unsaturated ketones has been accomplished using benzyl and tert ‐butyl mercaptans as the sulfur‐centered nucleophiles. Optically active products are obtained in high yields and good to excellent stereocontrol (up to 96 % ee ) from a large variety of enones. Central to these studies has been the use of the catalytic primary amine salt A , derived from 9‐amino‐(9‐deoxy)‐ epi ‐hydroquinine and D ‐ N ‐Boc‐phenylglycine, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis with enones.