Enantioselective Tandem Oxidation/Michael-Aldol Approaches to Tetrasubstituted Cyclohexanes

Nirmal K Rana; Harshit Joshi; Rupesh K Jha; Vinod K Singh

doi:10.1002/chem.201605999

Enantioselective Tandem Oxidation/Michael-Aldol Approaches to Tetrasubstituted Cyclohexanes

Chemistry. 2017 Feb 10;23(9):2040-2043. doi: 10.1002/chem.201605999. Epub 2017 Jan 20.

Authors

Nirmal K Rana¹, Harshit Joshi², Rupesh K Jha², Vinod K Singh^{1

2}

Affiliations

¹ Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, M.P.-, 462 066, India.
² Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, U.P.-, 208 016, India.

PMID: 28012254
DOI: 10.1002/chem.201605999

Abstract

Enantioselective tandem Michael-aldol and oxidative Michael-aldol approaches have been achieved for the formation of diversely substituted cyclohexanes in total regio-, diastereo- and enantioselective fashion. The presence of nitro, hydroxy and keto groups in the product provides a wide scope for further structural transformations. Furthermore, the utility of the catalytic process is demonstrated in the context of enantioselective formal synthesis of ABT-341, a DPP4 inhibitor.

Keywords: ABT-341; Michael-aldol; asymmetric synthesis; oxidation; tetrasubstituted cyclohexane.