Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenes via cyclopropanol intermediates.
Chem Commun (Camb)
; 54(22): 2800-2803, 2018 Mar 13.
Article
em En
| MEDLINE
| ID: mdl-29489006
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.
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MEDLINE
Idioma:
En
Ano de publicação:
2018
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Article