A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester

Guoxia Han; Victor J. Hruby

doi:10.1016/S0040-4039(01)00719-5

A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester

Guoxia Han, Victor J. Hruby

Chemistry and Biochemistry

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

13 Scopus citations

Abstract

Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.

Original language	English (US)
Pages (from-to)	4281-4283
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(01)00719-5
State	Published - Jun 25 2001

Keywords

Conjugate addition
Copper reagents
Copper(I) bromide dimethylsulfide complex
Copper(I) cyanide (CuCN)
Difficult reactions
Trimethylsilyl chloride (TMSCl)
α,β-unsaturated substrates with oxygen substitution at γ,δ-positions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(01)00719-5

Cite this

@article{0e5d14b9ecc34da6a00c5631fb40b04c,

title = "A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester",

abstract = "Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.",

keywords = "Conjugate addition, Copper reagents, Copper(I) bromide dimethylsulfide complex, Copper(I) cyanide (CuCN), Difficult reactions, Trimethylsilyl chloride (TMSCl), α,β-unsaturated substrates with oxygen substitution at γ,δ-positions",

author = "Guoxia Han and Hruby, {Victor J.}",

note = "Funding Information: We would like to thank Dr Steven H. Bertz and Dr Jon Rainier for helpful discussions. This research was supported in part by grants from the USPHS DK17420 and DA06284. Views expressed are those of the authors and are not necessary those of the USPHS.",

year = "2001",

month = jun,

day = "25",

doi = "10.1016/S0040-4039(01)00719-5",

language = "English (US)",

volume = "42",

pages = "4281--4283",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "26",

}

TY - JOUR

T1 - A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester

AU - Han, Guoxia

AU - Hruby, Victor J.

N1 - Funding Information: We would like to thank Dr Steven H. Bertz and Dr Jon Rainier for helpful discussions. This research was supported in part by grants from the USPHS DK17420 and DA06284. Views expressed are those of the authors and are not necessary those of the USPHS.

PY - 2001/6/25

Y1 - 2001/6/25

N2 - Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.

AB - Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.

KW - Conjugate addition

KW - Copper reagents

KW - Copper(I) bromide dimethylsulfide complex

KW - Copper(I) cyanide (CuCN)

KW - Difficult reactions

KW - Trimethylsilyl chloride (TMSCl)

KW - α,β-unsaturated substrates with oxygen substitution at γ,δ-positions

UR - http://www.scopus.com/inward/record.url?scp=0035948252&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035948252&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)00719-5

DO - 10.1016/S0040-4039(01)00719-5

M3 - Article

AN - SCOPUS:0035948252

SN - 0040-4039

VL - 42

SP - 4281

EP - 4283

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this