Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters

Kotaro Kikushima, Jeffrey C. Holder, Michele Gatti, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

157 Scopus citations

Abstract

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF(3))(2) and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.
Original languageEnglish (US)
Pages (from-to)6902-6905
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number18
DOIs
StatePublished - May 11 2011
Externally publishedYes

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