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Organocatalytic Highly Regio‐ and Enantioselective Umpolung Michael Addition Reaction of α‐Imino Esters
Author(s) -
Yoshida Yasushi,
Mino Takashi,
Sakamoto Masami
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703479
Subject(s) - umpolung , enantioselective synthesis , chemistry , catalysis , organocatalysis , michael reaction , organic chemistry , amino acid , organic synthesis , combinatorial chemistry , stereochemistry , biochemistry , nucleophile
The catalytic asymmetric umpolung reaction of ketimines is of great importance, because it can easily provide chiral amines bearing a tetrasubstituted carbon atom on its asymmetric center. Because amino acids with a tetrasubstituted carbon center are useful due to their wide applicability as pharmaceuticals and chiral building blocks, their enantioselective synthesis has great significance in organic synthesis. Herein, we demonstrate a metal‐free novel phase‐transfer‐catalyzed highly regio‐ and enantioselective umpolung Michael reaction of α‐imino esters, which provides amino acid derivatives in high yields with up to 98 % ee . The products are successfully converted into chiral amino acid derivative and δ‐lactone with high enantiopurity.