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Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

ABSTRACT: We describe highly enantioselective synthesis of beta-amino acid derivatives (1a-c) using asymmetric hydrogenation of alpha-aminomethylacrylates (2a-c), which contain a free basic N H group, as the key step. The alpha-aminomethylacrylates (2a-c) were prepared using the Baylis-Hillman reaction of an appropriate aldehyde with methyl acrylate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the allylic acetates (3a-b).

SUBMITTER: Qiu L

PROVIDER: S-EPMC2040417 | biostudies-literature | 2007 Oct

REPOSITORIES: biostudies-literature

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Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

Qiu Liqin L Prashad Mahavir M Hu Bin B Prasad Kapa K Repic Oljan O Blacklock Thomas J TJ Kwong Fuk Yee FY Kok Stanton H L SH Lee Hang Wai HW Chan Albert S C AS

Proceedings of the National Academy of Sciences of the United States of America 20071017 43

We describe highly enantioselective synthesis of beta-amino acid derivatives (1a-c) using asymmetric hydrogenation of alpha-aminomethylacrylates (2a-c), which contain a free basic N H group, as the key step. The alpha-aminomethylacrylates (2a-c) were prepared using the Baylis-Hillman reaction of an appropriate aldehyde with methyl acrylate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the allylic acetates (3a-b). ...[more]

PMID: 17942689

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