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A New Motif for Lewis Base Catalysis: Asymmetric Reduction of β‐Enamino Esters
Author(s) -
Weickgenannt Andreas,
Oestreich Martin
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201100210
Subject(s) - lewis acids and bases , chemistry , amide , catalysis , combinatorial chemistry , stereochemistry , organic chemistry
Reduced to the basics: Activation of Lewis acidic Cl 3 SiH with chiral amide‐based Lewis bases allows for the stereocontrolled reduction of several types of β‐enamino esters (see scheme). By this, the new motif of α‐acetoxy β‐enamino esters is transformed into α‐hydroxy β‐amino acids, a transformation still unknown in transition metal‐catalyzed hydrogenation. PMP=4‐methoxyphenyl.