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Enantiopure Monoprotected cis-1,2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis



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DACH to the future: A practical, one-step method for the highly enantioselective derivatization of cis-1,2-diaminocyclohexane (DACH), with diallyl carbonate as the acylating agent and Candida antarctica lipase B as catalyst is described. From the resulting enantiopure mono-N-alloc-cis-DACH, a series of derivatives are synthesized. The cis-DACH-derived sulfonamide catalysts gives high chemical yield, diastereo- and enantioselectivity in a direct aldol reaction.