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

Bowman Potter, Emma K. Edelstein and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu

B. Potter, E. K. Edelstein, J. P. Morken, Org. Lett., 2016, 18, 3286-3289.

DOI: 10.1021/acs.orglett.6b01580 (free Supporting Information)


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Abstract

The Suzuki-Miyaura cross-coupling with chiral γ,γ-disubstituted allylboronates provides nonracemic compounds with quaternary centers with high regioselectivity and enantiospecificity in the presence of RuPhos ligand. The reaction occurs by transmetalation with allyl migration, followed by rapid reductive elimination.

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Key Words

allylation (arenes, alkenes)


ID: J54-Y2016