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Highly Efficient Diastereoselective Reduction of α-Fluoroimines

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journal contribution
posted on 21.05.2010, 00:00 by Roy M. Malamakal, Whitney R. Hess, Todd A. Davis
A highly selective reduction of α-fluoroimines to the corresponding β-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 β-fluorinated amines in good yields and selectivity.