Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

David S. Hart; Li Qiang Sun; Alan P. Kozikowski

doi:10.1016/0040-4039(95)01648-2

Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

David S. Hart, Li Qiang Sun, Alan P. Kozikowski

School of Medicine

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

13 Scopus citations

Abstract

Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction. Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.

Original language	English (US)
Pages (from-to)	7787-7790
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	43
DOIs	https://doi.org/10.1016/0040-4039(95)01648-2
State	Published - Oct 23 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)01648-2

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title = "Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams",

abstract = "Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction. Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.",

author = "Hart, {David S.} and Sun, {Li Qiang} and Kozikowski, {Alan P.}",

year = "1995",

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T1 - Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

AU - Hart, David S.

AU - Sun, Li Qiang

AU - Kozikowski, Alan P.

PY - 1995/10/23

Y1 - 1995/10/23

N2 - Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction. Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.

AB - Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction. Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.

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U2 - 10.1016/0040-4039(95)01648-2

DO - 10.1016/0040-4039(95)01648-2

M3 - Article

AN - SCOPUS:0028885957

SN - 0040-4039

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SP - 7787

EP - 7790

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

Abstract

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