The Kulinkovich cyclopropanation reaction provides a flexible and convenient method for the synthesis of cyclopropanols. Together with the diverse chemistry of the cyclopropanol unit, it offers access to a wide range of functionalised unsaturated and saturated compounds. The successful use in the synthesis of natural compounds is outlined in this perspective.
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Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenes via cyclopropanol intermediates.
Chem Commun (Camb)
March 2018
Laboratory of Steroids, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich 5/2, Minsk 220141, Belarus.
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.
View Article and Find Full Text PDFThe Kulinkovich hydroxycyclopropanation reaction in natural product synthesis.
Org Biomol Chem
October 2012
University of Auckland, School of Chemical Sciences, 23 Symonds Street, Auckland 1043, New Zealand.
The Kulinkovich cyclopropanation reaction provides a flexible and convenient method for the synthesis of cyclopropanols. Together with the diverse chemistry of the cyclopropanol unit, it offers access to a wide range of functionalised unsaturated and saturated compounds. The successful use in the synthesis of natural compounds is outlined in this perspective.
View Article and Find Full Text PDFStereochemistry of cyclopropane formation involving group IV organometallic complexes.
J Am Chem Soc
February 2004
Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA.
The reaction of (Z)-HDC=CHCH(OCH(3))C(6)H(5) (1) with Cp(2)Zr(D)Cl followed by BF(3).OEt(2) gave phenylcyclopropanes 3a and 3b, both having cis deuterium. This stereochemical outcome requires inversion of configuration at the carbon bound to zirconium and is consistent with a "W-shaped" transition state structure for cyclopropane formation.
View Article and Find Full Text PDFDiastereoselective synthesis of trans-1,2-dialkylcyclopropanols by the Kulinkovich hydroxycyclopropanation of homoallylic alcohols.
Angew Chem Int Ed Engl
June 2002
Department of Chemistry, University of Alabama, Tuscaloosa, AL 35487, USA.
A theoretical study on the mechanism and diastereoselectivity of the Kulinkovich hydroxycyclopropanation reaction.
J Am Chem Soc
June 2001
Department of Chemistry, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China.
A detailed mechanism for the Kulinkovich hydroxycyclopropanation reaction has been explored with density functional theory calculations on the reactions between R(1)COOMe and Ti(OMe)(2)(CH(2)CHR(2)) (R(1) and R(2) are hydrogen and alkyl groups). Addition of ester to titanacyclopropane is found to be fast, exothermic, and irreversible. It has a preference for the alpha-addition manifold over the beta-addition manifold in which its cycloinsertion transition states suffer from the steric repulsion between the R(2) and ester.
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