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

Berkessel A. | Zendy; Ong M.C. | Zendy; Nachi M. | Zendy; Neudörfl J.M. | Zendy

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

Author(s) -

Berkessel A.,

Ong M.C.,

Nachi M.,

Neudörfl J.M.

Publication year - 2010

Publication title -

chemcatchem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.497

H-Index - 106

eISSN - 1867-3899

pISSN - 1867-3880

DOI - 10.1002/cctc.201000104

Subject(s) - enantiopure drug , organocatalysis , chemistry , enantioselective synthesis , combinatorial chemistry , stereochemistry , organic chemistry , catalysis

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.

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