Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands

Kimberly S. Petersen, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center. © 2011 Elsevier Ltd. All rights reserved.
Original languageEnglish (US)
Pages (from-to)4352-4357
Number of pages6
JournalTetrahedron
Volume67
Issue number24
DOIs
StatePublished - Jun 2011
Externally publishedYes

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