Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions |
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Authors: | Yang Dexi Belardi Justin K Micalizio Glenn C |
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Affiliation: | a Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, FL 33458, United States b Department of Chemistry, Yale University, New Haven, CT 06520, United States |
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Abstract: | Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. |
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Keywords: | Stereoselective synthesis Reductive cross-coupling Allylic alcohol Titanium alkoxide Quaternary center |
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