Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols Using a Guanidine-Catalyzed Tandem Henry–Michael Reaction

A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry–-Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki–Sugimura guanidine.

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Bibliographic Details
Published in:Journal of organic chemistry 2013-04, Vol.78 (8), p.4153-4157
Main Authors: Dai, Qipu, Huang, Huicai, Cong-Gui Zhao, John
Format: Article
Language:English
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Summary:A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry–-Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki–Sugimura guanidine.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4001806