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Stereocontrol in Synthesis of Homoallylic Amines. Syn Selective Direct Allylation of Hydrazones with Allylboronic Acids

Arindam Das, Rauful Alam, Lars Eriksson and Kálmán J. Szabó*

*Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden, Email: kalmanorgan.su.se

A. Das, R. Alam, L. Eriksson, K. J. Szabo, Org. Lett., 2014, 16, 3808-3811.

DOI: 10.1021/ol501699x



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Abstract

The reaction of allylboronic acids with acyl hydrazones proceeds with very high syn selectivity to afford homoallylic amine derivatives. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. The excellent syn stereochemistry, which is the opposite of the stereochemistry observed for allylboration of imines, can be explained by chelation control of the acyl hydrazone and the B(OH)2 moiety.

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Key Words

homoallylic hydrazines


ID: J54-Y2014