Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 43, Pages 15606-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9076815
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Government of Ontario
- Canadian Foundation for Innovation
- Ontario Innovation Trust
- University of Waterloo
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The modification of sp(3)-hybridized carbon centers through Pd-catalyzed reductive cleavage of unstrained carbon-carbon a bonds is described. From the hydrogenolysis of benzyl Meldrum's acids bearing an all-carbon benzylic quaternary center, Meldrum's acid and aromatics substituted with a tertiary benzylic stereocenter were obtained in good to excellent yields. Mechanistic studies showed that the reductive cleavage of enantioenriched benzylic quaternary centers proceeded with inversion of configuration, supporting a loose S(N)2 pathway.
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