Synthesis of Diastereomeric 3,6-Diaminobicyclo[3.1.0]hexane Derivatives: A Stereocomplementary Approach

Elmar Vilsmaier; Joachim Fath; Gerhard Maas

doi:10.1055/s-1991-28406

Synthesis 1991; 1991(12): 1142-1146
DOI: 10.1055/s-1991-28406

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Synthesis of Diastereomeric 3,6-Diaminobicyclo[3.1.0]hexane Derivatives: A Stereocomplementary Approach

Elmar Vilsmaier^* , Joachim Fath, Gerhard Maas

^*Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Str., D-6750 Kaiserslautern, Germany

Abstract

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Diastereomeric (1α,3β,5α,6β)- and (1α,3α,5α,6β)-diaminobicyclo [3.1.0]hexane-6-carbonitriles 12 and 16 were synthesized with high stereoselectivity from 1,4-cyclohexanedione monoacetal 6 via chloroenamines 17 and 18, respectively. The sequence of reaction of 6 with a cyclic amine to give an enamine, chlorination with N-chlorosuccinimide and subsequent cyclopropanation with cyanide ion in the presence of a phase-transfer catalyst, cleavage of the acetal function followed by reductive amination, leads to 12. Changing the order of these synthetic steps allows an easy approach to 16. The configurations of 12 and 16 were established by ¹H- and ¹³C-NMR data and an X-ray structural analysis of 16b.

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