Organic Letters, volume 12, issue 7, pages 1552-1555

An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)₂, NMO, and Catalytic OsO₄

K C Nicolaou ¹

Vikrant A Adsool ¹

Christopher R H Hale ¹

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Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and the Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093

University of California, San Diego

Scripps Research

Publication type: Journal Article

Publication date: 2010-02-25

American Chemical Society (ACS)

Journal: Organic Letters

scimago Q1

wos Q1

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/ol100290a

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PubMed ID: 20192259

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

PhI(OAc)(2) in the presence of OsO(4) (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with alpha-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO(4) (cat.), 2,6-lutidine, and PhI(OAc)(2).

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Nicolaou K. C., Adsool V. A., Hale C. R. H. An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4 // Organic Letters. 2010. Vol. 12. No. 7. pp. 1552-1555.

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RIS Copy

TY - JOUR

DO - 10.1021/ol100290a

UR - https://doi.org/10.1021/ol100290a

TI - An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4

T2 - Organic Letters

AU - Nicolaou, K C

AU - Adsool, Vikrant A

AU - Hale, Christopher R H

PY - 2010

DA - 2010/02/25

PB - American Chemical Society (ACS)

SP - 1552-1555

IS - 7

VL - 12

PMID - 20192259

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2010_Nicolaou,

author = {K C Nicolaou and Vikrant A Adsool and Christopher R H Hale},

title = {An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4},

journal = {Organic Letters},

year = {2010},

volume = {12},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/ol100290a},

number = {7},

pages = {1552--1555},

doi = {10.1021/ol100290a}

}

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Nicolaou, K. C., et al. “An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4.” Organic Letters, vol. 12, no. 7, Feb. 2010, pp. 1552-1555. https://doi.org/10.1021/ol100290a.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)