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

Kimberly S. Petersen; Brian M. Stoltz

doi:10.1016/j.tet.2011.04.046

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

Kimberly S. Petersen, Brian M. Stoltz

Research output: Contribution to journal › Article › peer-review

31 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 language	English (US)
Pages (from-to)	4352-4357
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2011.04.046
State	Published - Jun 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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10.1016/j.tet.2011.04.046

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

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. {\textcopyright} 2011 Elsevier Ltd. All rights reserved.",

author = "Petersen, {Kimberly S.} and Stoltz, {Brian M.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2011",

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doi = "10.1016/j.tet.2011.04.046",

language = "English (US)",

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AU - Petersen, Kimberly S.

AU - Stoltz, Brian M.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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Y1 - 2011/6

N2 - 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.

AB - 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.

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UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402011005539

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DO - 10.1016/j.tet.2011.04.046

M3 - Article

SN - 0040-4020

VL - 67

SP - 4352

EP - 4357

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

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

Abstract

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