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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.