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Highly efficient diastereoselective reduction of alpha-fluoroimines.

ABSTRACT: A highly selective reduction of alpha-fluoroimines to the corresponding beta-fluoroamines has been developed utilizing trichlorosilane as the reductant. The key aspect of this reaction is the ability of fluorine and nitrogen to activate organosilanes leading to high diastereoselectivity (>100:1) in the product distribution. This new method provides a new avenue for the diastereoselective synthesis of beta-fluorinated amines in good yields and selectivity.

SUBMITTER: Malamakal RM

PROVIDER: S-EPMC2929650 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Highly efficient diastereoselective reduction of alpha-fluoroimines.

Malamakal Roy M RM Hess Whitney R WR Davis Todd A TA

Organic letters 20100501 10

A highly selective reduction of alpha-fluoroimines to the corresponding beta-fluoroamines has been developed utilizing trichlorosilane as the reductant. The key aspect of this reaction is the ability of fluorine and nitrogen to activate organosilanes leading to high diastereoselectivity (>100:1) in the product distribution. This new method provides a new avenue for the diastereoselective synthesis of beta-fluorinated amines in good yields and selectivity. ...[more]

PMID: 20408600

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