Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis

Bill Morandi; Zachary K. Wickens; Robert H. Grubbs

doi:10.1002/ange.201303587

Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis

Bill Morandi, Zachary K. Wickens, Robert H. Grubbs

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

52 Scopus citations

Abstract

Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.

Original language	English (US)
Pages (from-to)	9933-9936
Number of pages	4
Journal	Angewandte Chemie
Volume	125
Issue number	37
DOIs	https://doi.org/10.1002/ange.201303587
State	Published - Jul 26 2013
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We gratefully acknowledge financial support from the King Abdullah University of Science and Technology Centre in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis",

abstract = "Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.",

author = "Bill Morandi and Wickens, {Zachary K.} and Grubbs, {Robert H.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge financial support from the King Abdullah University of Science and Technology Centre in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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T1 - Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis

AU - Morandi, Bill

AU - Wickens, Zachary K.

AU - Grubbs, Robert H.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge financial support from the King Abdullah University of Science and Technology Centre in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2013/7/26

Y1 - 2013/7/26

N2 - Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.

AB - Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.

UR - http://hdl.handle.net/10754/599484

UR - http://doi.wiley.com/10.1002/ange.201303587

U2 - 10.1002/ange.201303587

DO - 10.1002/ange.201303587

M3 - Article

SN - 0044-8249

VL - 125

SP - 9933

EP - 9936

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 37

ER -

Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis

Abstract

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