CaltechAUTHORS
Published June 17, 2011 | Version public
Journal Article Metadata-only

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

Creators

  • 1. ROR icon California Institute of Technology

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.

Additional Information

© 2011 Elsevier Ltd. Received 28 February 2011; revised 11 April 2011; accepted 13 April 2011. Available online 23 April 2011. Dedicated to Professor F. Dean Toste on the receipt of the 2011 Tetrahedron Young Investigator Award. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST).

Additional details

Identifiers

Eprint ID
24322
DOI
10.1016/j.tet.2011.04.046
Resolver ID
CaltechAUTHORS:20110706-135043254

Related works

Describes
10.1016/j.tet.2011.04.046 (DOI)

Funding

King Abdullah University of Science and Technology (KAUST)
KUS-11-006-02

Dates

Created
2011-07-13
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field