Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

ABSTRACT: Regio-, diastereo-, and enantioselective coupling reactions between imines and allylic alcohols have been developed. These coupling reactions deliver complex homoallylic amine products through a convergent C-C bond forming process that does not proceed through intermediate allylic organometallic reagents. In general, convergent coupling, by exposure of an allylic alkoxide to a preformed Ti-imine complex, occurs with allylic transposition in a predictable and stereocontrolled manner. While simple diastereoselection in these reactions is high, delivering anti-products with ≥20:1 selectivity, the organometallic transformation described is compatible with a diverse range of functionality and substrates (including aliphatic and aromatic imines, allylic silanes, trisubstituted alkenes, vinyl- an

SUBMITTER: Chen MZ 

PROVIDER: S-EPMC2993781 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature