Tetrahedron: Asymmetry

Diastereo-and enantioselective synthesis of cis-2-hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination

G Lauktien, FJ Volk, AW Frahm

Index: Lauktien, Gerhard; Volk, Franz-J; Frahm, August W. Tetrahedron Asymmetry, 1997 , vol. 8, # 20 p. 3457 - 3466

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Citation Number: 31

Abstract

A series of homochiral cis-2-alkoxy-and 2-aryloxycyclohexanamines 5b-5e has been synthesised by means of asymmetric reductive amination of the corresponding racemic 2- oxygenated cyclohexanones 2 with ee-values ranging from 95 to> 99%. The respective 2- hydroxy and 2-cyclohexyl derivatives 5g-5h have been prepared from the 2- phenoxycyclohexanamine 4e. Relative and absolute stereochemistry has been elucidated.

~62%

~68%

~73%

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