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

Chemical Communications : Chem Comm
Maryia V BarysevichVladimir A Khripach

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.

References

Jul 10, 2003·Chemical Reviews·Oleg G Kulinkovich
Feb 16, 2008·Organic Letters·Katie A Keaton, Andrew J Phillips
Aug 14, 2012·Organic & Biomolecular Chemistry·Isabell Haym, Margaret A Brimble
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May 11, 2013·Chemical Communications : Chem Comm·David Rosa, Arturo Orellana
Jul 25, 2013·Chemistry, an Asian Journal·Shao-Gang Li, Yikang Wu
Dec 10, 2014·Current Topics in Medicinal Chemistry·Gonzalo PazosManuel Pérez
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May 13, 2017·Angewandte Chemie·Rafael CanoGerard P McGlacken
Aug 23, 2017·Journal of the American Chemical Society·Brendon T Sargent, Erik J Alexanian
Dec 6, 2017·Angewandte Chemie·Łukasz WoźniakPaolo Melchiorre

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Citations

Dec 4, 2019·Organic & Biomolecular Chemistry·Qiang LiuXiaoxia Wang
Aug 28, 2020·Chemical Society Reviews·Manfred Manßen, Laurel L Schafer
Apr 17, 2019·Nature Reviews. Chemistry·Evan P BeaumierIan A Tonks
Oct 22, 2020·Chemical Reviews·Tyler R McDonaldSophie A L Rousseaux

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Methods Mentioned

BETA
NMR

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