Stereoselective CrCl2-mediated condensation of aldehydes with functionalized 1,1,1-trichlorides: Synthesis of trisubstituted (Z)-chloroolefins

J R Falck; Anish Bandyopadhyay; D. K. Barma; Dong Soo Shin; Abhijit Kundu; R. V. Krishna Kishore

doi:10.1016/j.tetlet.2004.02.101

Stereoselective CrCl₂-mediated condensation of aldehydes with functionalized 1,1,1-trichlorides: Synthesis of trisubstituted (Z)-chloroolefins

J R Falck, Anish Bandyopadhyay, D. K. Barma, Dong Soo Shin, Abhijit Kundu, R. V. Krishna Kishore

Biochemistry

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

14 Scopus citations

Abstract

The CrCl₂-mediated condensation of aldehydes 1 with a variety of functionalized 1,1,1-trichlorides 2 affords trisubstituted chloroolefins 4 in excellent yields and generally high Z-stereoselectivity. The intermediate dichlorohydrin adducts 3 can be isolated in good yields under conditions of limited reagent and reduced temperature.

Original language	English (US)
Pages (from-to)	3039-3042
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.101
State	Published - Apr 5 2004

Keywords

Chromium
Condensations
Olefination
Stereocontrol

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.02.101

Cite this

@article{c6c57023c4ff4904b236395128602c5e,

title = "Stereoselective CrCl2-mediated condensation of aldehydes with functionalized 1,1,1-trichlorides: Synthesis of trisubstituted (Z)-chloroolefins",

abstract = "The CrCl2-mediated condensation of aldehydes 1 with a variety of functionalized 1,1,1-trichlorides 2 affords trisubstituted chloroolefins 4 in excellent yields and generally high Z-stereoselectivity. The intermediate dichlorohydrin adducts 3 can be isolated in good yields under conditions of limited reagent and reduced temperature.",

keywords = "Chromium, Condensations, Olefination, Stereocontrol",

author = "Falck, {J R} and Anish Bandyopadhyay and Barma, {D. K.} and Shin, {Dong Soo} and Abhijit Kundu and {Krishna Kishore}, {R. V.}",

note = "Funding Information: Financial support provided by the CNRS, the Robert A. Welch Foundation, and NIH (GM31278, DK38226).",

year = "2004",

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doi = "10.1016/j.tetlet.2004.02.101",

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T1 - Stereoselective CrCl2-mediated condensation of aldehydes with functionalized 1,1,1-trichlorides

T2 - Synthesis of trisubstituted (Z)-chloroolefins

AU - Falck, J R

AU - Bandyopadhyay, Anish

AU - Barma, D. K.

AU - Shin, Dong Soo

AU - Kundu, Abhijit

AU - Krishna Kishore, R. V.

N1 - Funding Information: Financial support provided by the CNRS, the Robert A. Welch Foundation, and NIH (GM31278, DK38226).

PY - 2004/4/5

Y1 - 2004/4/5

N2 - The CrCl2-mediated condensation of aldehydes 1 with a variety of functionalized 1,1,1-trichlorides 2 affords trisubstituted chloroolefins 4 in excellent yields and generally high Z-stereoselectivity. The intermediate dichlorohydrin adducts 3 can be isolated in good yields under conditions of limited reagent and reduced temperature.

AB - The CrCl2-mediated condensation of aldehydes 1 with a variety of functionalized 1,1,1-trichlorides 2 affords trisubstituted chloroolefins 4 in excellent yields and generally high Z-stereoselectivity. The intermediate dichlorohydrin adducts 3 can be isolated in good yields under conditions of limited reagent and reduced temperature.

KW - Chromium

KW - Condensations

KW - Olefination

KW - Stereocontrol

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