Article

Alkylation of a chiral hydrazone by means of asymmetric addition of Grignard reagents to the carbon-nitrogen double bond.

Hiroshi TakahashiInstitute of Medicinal Chemistry, Hoshi University, Kaken Pharmaceutical Co., LtdYuji SuzukiInstitute of Medicinal Chemistry, Hoshi University, Kaken Pharmaceutical Co., Ltd

Chemical and Pharmaceutical Bulletinjournal1983en

ABI

Abstract

A chiral hydrazone, (E)-(S)-N'-benzylidene-N, 3-dimethyl-2-hydrazinobutanol (6), was synthesized from (S)-valinol. Compound 6 was reacted with Grignard reagents to give optically pure (2S, 1'S)-N, 3-dimethyl-N'-1'-phenylalkyl-2-hydrazinobutanols (7a and 7b). However, N'-2'-aryl-1'-phenylethyl-N, 3-dimethyl-2-hydrazinobutanols (7c and 7d) were each obtained as a mixture of two diastereomers. Nitrogen-nitrogen bonds of 7a and 7b were cleaved by hydrogenolysis to give (S)-1-phenylalkylamines (8a and 8b), and their absolute configurations and optical purities were confirmed. These reactions were assumed to proceed via the chelated sixmembered ring intermediates.

Topics

Analytical Chemistry and Chromatography Chemical Reaction Mechanisms Asymmetric Synthesis and Catalysis

Identifiers

DOI: 10.1248/cpb.31.4295

Citations and references

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