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Synfacts 2005(0): 0066-0066  
DOI: 10.1055/s-2005-869925
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Rh-Catalyzed Addition of Arylboron Compounds to Sulfinimines

Contributor(s): Paul Knochel, Andrei Gavryushin
Y. Bolshan, R. A. Batey*
University of Toronto, Canada
A Room-Temperature Protocol for the Rhodium(I)-Catalyzed Addition of Arylboron Compounds to Sulfinimines
Org. Lett.  2005,  7:  1481-1484  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

sulfinimines - arylboronic acids - addition

Significance

The synthesis of chiral benzylic amines is an important task, since these compounds often possess biologic activity. Usual addition of an organometallic reagent to imines is limited by various factors including functional group compatibility and use of highly sensitive reagents. This protocol offers very mild reaction conditions and is advantageous due to the stability and availability of the reactants.

Comment

The use of arylboronic acids in 1,2-addition is relatively less developed, although there is a number of advantages, mainly the possibility for storing the boron compound. The used chiral auxiliary is readily accessible. Whereas many methods are known for the enantioselective addition to imines, they often require handling of sensitive organometallic reagents.

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