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Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

ABSTRACT: The catalytic Suzuki-Miyaura cross-coupling with chiral ?,?-disubstituted allylboronates in the presence of RuPhos ligand occurs with high regioselectivity and enantiospecificity, furnishing nonracemic compounds with quaternary centers. Mechanistic experiments suggest that the reaction occurs by transmetalation with allyl migration, followed by rapid reductive elimination.

SUBMITTER: Potter B 

PROVIDER: S-EPMC5510877 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

Potter Bowman B   Edelstein Emma K EK   Morken James P JP  

Organic letters 20160616 13

The catalytic Suzuki-Miyaura cross-coupling with chiral γ,γ-disubstituted allylboronates in the presence of RuPhos ligand occurs with high regioselectivity and enantiospecificity, furnishing nonracemic compounds with quaternary centers. Mechanistic experiments suggest that the reaction occurs by transmetalation with allyl migration, followed by rapid reductive elimination. ...[more]

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