Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate with aryl alkyl ketones by employing Sn(OSO(2)CF(3))(2) and N-ethylpiperidine.
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Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis.
J Am Chem Soc
December 2009
Department of Chemistry, 930 North University Avenue, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
A unified approach to the pyrrolidine triacid natural products isodomoic acids G and H has been developed. Total syntheses of both natural products were completed, and determination of the correct stereostructure of isodomoic acid G was established by comparing 5'-(R) and 5'-(S) isomers to a sample of authentic material. A nickel-catalyzed cyclization constructs the pyrrolidine ring while simultaneously establishing either the E or Z stereochemistry of an exocyclic tetrasubstituted alkene.
View Article and Find Full Text PDFUnusual effects in the pd-catalyzed asymmetric allylic alkylations: synthesis of chiral chromans.
J Am Chem Soc
August 2003
Department of Chemistry, Stanford Univeristy, Stanford, California 94305-5080, USA.
An examination of earlier reports of poor-to-modest results using Pd-catalyzed asymmetric allylic alkylations (AAA) to effect cyclization to form tetrasubstituted carbons reveals several novel factors that can influence this class of reactions. Thus, carboxylate has a major effect on such cyclizations wherein the ee increases from 14% ee favoring the S with no carboxylate to 84% ee favoring the R enantiomer in the presence of 1 equiv of carboxylate. Changing the double bond geometry from E to Z further increases the ee to 97%.
View Article and Find Full Text PDFStereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction.
Chem Pharm Bull (Tokyo)
September 2002
Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Japan.
Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate with aryl alkyl ketones by employing Sn(OSO(2)CF(3))(2) and N-ethylpiperidine.
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