Premium
Phase‐Transfer‐Catalyzed Enantioselective Mannich Reaction of Malonates with α‐Amido Sulfones
Author(s) -
Fini Francesco,
Bernardi Luca,
Herrera Raquel P.,
Pettersen Daniel,
Ricci Alfredo,
Sgarzani Valentina
Publication year - 2006
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.200600250
Subject(s) - chemistry , enantioselective synthesis , organocatalysis , catalysis , mannich reaction , potassium carbonate , ammonium , adduct , organic chemistry , combinatorial chemistry , medicinal chemistry
The highly enantioselective reaction between in situ generated, Cbz‐protected azomethines and malonates in the presence of 150 mol % of potassium carbonate (50 % w/w) and 1 mol % of quinine‐derived quaternary ammonium bromides as phase‐transfer organocatalysts has been developed. This study reports a novel approach for the asymmetric Mannich‐type reaction and a wide range of azomethines, including those derived from enolizable aldehydes, is tolerated by the present system. The adducts, obtained in excellent yields with ee up to 98 %, are suitable precursors of optically pure β‐amino acids.