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Synfacts 2005(2): 0236-0236
DOI: 10.1055/s-2005-916085
DOI: 10.1055/s-2005-916085
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Homoallylic Amines by Hydrozirconation-Imine Addition of Allenes
P. Wipf*, J. G. Pierce
University of Pittsburgh, USA
Further Information
Publication History
Publication Date:
25 October 2005 (online)
Significance
Hydrozirconation of allenes followed by transmetallation to dialkylzinc and then addition to aldimines gave homoallylic amines as predominantly the syn-substituted product A. A cyclic transition state was proposed to rationalize the highly syn-selective substituted products. Examples of the reaction include silylated and stannylated homoallylic amines allowing further derivatisation by cross-coupling or allylation.