Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenes via cyclopropanol intermediates†
Maryia V.
Barysevich, 
a
Volha V.
Kazlova,
a
Aliaksandr G.
Kukel,
a
Aliaksandra I.
Liubina,
a
Alaksiej L.
Hurski,
*a
Vladimir N.
Zhabinskii
a
and
Vladimir A.
Khripach
a
a
Volha V.
Kazlova,
a
Aliaksandr G.
Kukel,
a
Aliaksandra I.
Liubina,
a
Alaksiej L.
Hurski,
*a
Vladimir N.
Zhabinskii
a
and
Vladimir A.
Khripach
a
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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