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

Article abstract of DOI:10.1016/S0957-4166(97)00456-4

A series of homochiral cis-2-alkoxy- and 2-aryloxyeyclohexanamines 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.