Synfacts 2007(5): 0541-0541  
DOI: 10.1055/s-2007-968407
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Sequential α-Amination-Horner-Wadsworth-Emmons Olefination

Contributor(s): Benjamin List, Daniela Kampen
S. P. Kotkar, V. B. Chavan, A. Sudalai
National Chemical Laboratory, Pune, India
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Publication History

Publication Date:
24 April 2007 (online)


An organocatalytic asymmetric one-pot procedure for the construction of γ-­amino-α,β-unsaturated esters has been developed. α-Amination of aldehydes 1 using dibenzyl azodicarboxylate (DBAD) in the presence of 10 mol% of l-proline was followed by subsequent Horner-Wadsworth-Emmons olefination to provide products of type 2 in high overall yields and enantioselectivities. γ-Amino-α,β-unsaturated esters 2 can be transformed into chiral 2-pyrrolidones 3 and 4 under hydrogenation conditions.