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Organocatalytic enantioselective olefin aminofluorination.

ABSTRACT: Chiral beta-fluoroamines are increasingly prevalent in medicinal compounds, but there are few efficient methods to access them from achiral starting materials. To address this, a multicomponent organocascade reaction was developed in which chiral alpha-fluoro-beta-amino aldehydes were generated in a single flask from achiral alpha,beta-unsaturated aldehydes (2), using catalyst 12a. Conversions up to 85%, dr's up to 98:2 and ee's up to 99% of the corresponding alcohol (9) were achieved in this reaction.

SUBMITTER: Appayee C

PROVIDER: S-EPMC2946328 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Organocatalytic enantioselective olefin aminofluorination.

Appayee Chandrakumar C Brenner-Moyer Stacey E SE

Organic letters 20100801 15

Chiral beta-fluoroamines are increasingly prevalent in medicinal compounds, but there are few efficient methods to access them from achiral starting materials. To address this, a multicomponent organocascade reaction was developed in which chiral alpha-fluoro-beta-amino aldehydes were generated in a single flask from achiral alpha,beta-unsaturated aldehydes (2), using catalyst 12a. Conversions up to 85%, dr's up to 98:2 and ee's up to 99% of the corresponding alcohol (9) were achieved in this re ...[more]

PMID: 20575576

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