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Updated: Jun 8, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Catalytic asymmetric synthesis of chiral allylic esters
Jeffrey S Cannon1, Stefan F Kirsch, Larry E Overman
1Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Abstract:
A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective S(N)2' substitution with a variety of carboxylic acids in the presence of the palladium(II) catalyst (R(p),S)-di-μ-acetatobis[(η(5)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl-1-C,3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium, (R(p),S)-[COP-OAc](2), or its enantiomer. The scope and limitations of this useful catalytic asymmetric allylic esterification are defined.
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