Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenes via cyclopropanol intermediates

Maryia V Barysevich; Volha V Kazlova; Aliaksandr G Kukel; Aliaksandra I Liubina; Alaksiej L Hurski; Vladimir N Zhabinskii; Vladimir A Khripach

doi:10.1039/c8cc00888d

Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenes via cyclopropanol intermediates

Chem Commun (Camb). 2018 Mar 13;54(22):2800-2803. doi: 10.1039/c8cc00888d.

Authors

Maryia V Barysevich¹, Volha V Kazlova, Aliaksandr G Kukel, Aliaksandra I Liubina, Alaksiej L Hurski, Vladimir N Zhabinskii, Vladimir A Khripach

Affiliation

¹ Laboratory of Steroids, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich 5/2, Minsk 220141, Belarus. AHurski@iboch.by.

PMID: 29489006
DOI: 10.1039/c8cc00888d

Abstract

Alkenes bearing a stereocenter in the allylic position were found to undergo Kulinkovich hydroxycyclopropanation with good diastereoselectivity. For the isomerization of the resulting cyclopropanols to diastereomerically enriched α-methyl ketones, a new mild regioselective method has been developed. A sequence of stereoselective cyclopropanation and cyclopropanol ring opening was successfully employed for the construction of the C20 stereocenter in steroids.