Stereoselective dioxygenation of enoates

Patrick H. Dussault; Kevin R. Woller; Michael C. Hillier

doi:10.1016/S0040-4020(01)85363-1

Stereoselective dioxygenation of enoates

Patrick H. Dussault, Kevin R. Woller, Michael C. Hillier

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

25 Scopus citations

Abstract

The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.

Original language	English (US)
Pages (from-to)	8929-8940
Number of pages	12
Journal	Tetrahedron
Volume	50
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4020(01)85363-1
State	Published - 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{753c86410cef400bb41e391f3c809e76,

title = "Stereoselective dioxygenation of enoates",

abstract = "The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.",

author = "{H. Dussault}, Patrick and {R. Woller}, Kevin and {C. Hillier}, Michael",

note = "Funding Information: We gratefully acknowledge the American Cancer Society (CN-33 and CN-33a) for financial support, Professor Richard Shoemaker for valuable assistance with NMR studies aud Dr. Charles Ross for acquiring and refining the crystal structure of the minor alcohol.",

year = "1994",

doi = "10.1016/S0040-4020(01)85363-1",

language = "English (US)",

volume = "50",

pages = "8929--8940",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "30",

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TY - JOUR

T1 - Stereoselective dioxygenation of enoates

AU - H. Dussault, Patrick

AU - R. Woller, Kevin

AU - C. Hillier, Michael

N1 - Funding Information: We gratefully acknowledge the American Cancer Society (CN-33 and CN-33a) for financial support, Professor Richard Shoemaker for valuable assistance with NMR studies aud Dr. Charles Ross for acquiring and refining the crystal structure of the minor alcohol.

PY - 1994

Y1 - 1994

N2 - The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.

AB - The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.

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UR - http://www.scopus.com/inward/citedby.url?scp=0028101775&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)85363-1

DO - 10.1016/S0040-4020(01)85363-1

M3 - Article

AN - SCOPUS:0028101775

SN - 0040-4020

VL - 50

SP - 8929

EP - 8940

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -

Stereoselective dioxygenation of enoates

Abstract

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