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

Handle URI:
http://hdl.handle.net/10754/599133
Title:
Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands
Authors:
Petersen, Kimberly S.; Stoltz, Brian M.
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.
Citation:
Petersen KS, Stoltz BM (2011) Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands. Tetrahedron 67: 4352–4357. Available: http://dx.doi.org/10.1016/j.tet.2011.04.046.
Publisher:
Elsevier BV
Journal:
Tetrahedron
KAUST Grant Number:
KUS-11-006-02
Issue Date:
Jun-2011
DOI:
10.1016/j.tet.2011.04.046
Type:
Article
ISSN:
0040-4020
Sponsors:
This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST).
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Full metadata record

DC FieldValue Language
dc.contributor.authorPetersen, Kimberly S.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T13:53:29Zen
dc.date.available2016-02-25T13:53:29Zen
dc.date.issued2011-06en
dc.identifier.citationPetersen KS, Stoltz BM (2011) Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands. Tetrahedron 67: 4352–4357. Available: http://dx.doi.org/10.1016/j.tet.2011.04.046.en
dc.identifier.issn0040-4020en
dc.identifier.doi10.1016/j.tet.2011.04.046en
dc.identifier.urihttp://hdl.handle.net/10754/599133en
dc.description.abstractDescribed 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.en
dc.description.sponsorshipThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST).en
dc.publisherElsevier BVen
dc.subjectAsymmetric catalysisen
dc.subjectBaeyer-Villiger oxidationen
dc.subjectPalladiumen
dc.subjectPhosphinooxazoline ligandsen
dc.titlePalladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligandsen
dc.typeArticleen
dc.identifier.journalTetrahedronen
dc.contributor.institutionCalifornia Institute of Technology, Pasadena, United Statesen
kaust.grant.numberKUS-11-006-02en
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