First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions

Xin Xu; Dianjun Chen; Han Xun Wei; Guigen Li; Tom Ling Xiao; Daniel W. Armstrong

doi:10.1002/chir.10179

First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions

Xin Xu, Dianjun Chen, Han Xun Wei, Guigen Li, Tom Ling Xiao, Daniel W. Armstrong

Chemistry and Biochemistry

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

12 Scopus citations

Abstract

A new asymmetric approach to chiral β-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and α,β-acetylenic menthyl ester in dichloromethane at -23°C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.

Original language	English
Pages (from-to)	139-142
Number of pages	4
Journal	Chirality
Volume	15
Issue number	2
DOIs	https://doi.org/10.1002/chir.10179
State	Published - 2003

Keywords

Asymmetric aldol reaction
Baylis-Hillman adducts
Conjugate addition
Diethylaluminum iodide
Menthol auxiliary

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10.1002/chir.10179

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title = "First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions",

abstract = "A new asymmetric approach to chiral β-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and α,β-acetylenic menthyl ester in dichloromethane at -23°C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.",

keywords = "Asymmetric aldol reaction, Baylis-Hillman adducts, Conjugate addition, Diethylaluminum iodide, Menthol auxiliary",

author = "Xin Xu and Dianjun Chen and Wei, {Han Xun} and Guigen Li and Xiao, {Tom Ling} and Armstrong, {Daniel W.}",

year = "2003",

doi = "10.1002/chir.10179",

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pages = "139--142",

journal = "Chirality",

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T1 - First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions

AU - Xu, Xin

AU - Chen, Dianjun

AU - Wei, Han Xun

AU - Li, Guigen

AU - Xiao, Tom Ling

AU - Armstrong, Daniel W.

PY - 2003

Y1 - 2003

N2 - A new asymmetric approach to chiral β-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and α,β-acetylenic menthyl ester in dichloromethane at -23°C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.

AB - A new asymmetric approach to chiral β-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and α,β-acetylenic menthyl ester in dichloromethane at -23°C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.

KW - Asymmetric aldol reaction

KW - Baylis-Hillman adducts

KW - Conjugate addition

KW - Diethylaluminum iodide

KW - Menthol auxiliary

UR - http://www.scopus.com/inward/record.url?scp=0037255658&partnerID=8YFLogxK

U2 - 10.1002/chir.10179

DO - 10.1002/chir.10179

M3 - Article

C2 - 12520505

AN - SCOPUS:0037255658

SN - 0899-0042

VL - 15

SP - 139

EP - 142

JO - Chirality

JF - Chirality

IS - 2

ER -

First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions

Abstract

Keywords

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