Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation-aldehyde addition

Rachid Baati, D. K. Barma, J R Falck, Charles Mioskowski

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Cr(II)-induced condensation of CCl4 or CBr4 with an aldehyde stereospecifically generates an (E)-α-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.

Original languageEnglish (US)
Pages (from-to)2179-2181
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number12
DOIs
StatePublished - Mar 18 2002

Fingerprint

Aldehydes
Chromium
Condensation

Keywords

  • Alcohols
  • Alkenylation
  • Chromium
  • Stereocontrol
  • Vinylation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation-aldehyde addition. / Baati, Rachid; Barma, D. K.; Falck, J R; Mioskowski, Charles.

In: Tetrahedron Letters, Vol. 43, No. 12, 18.03.2002, p. 2179-2181.

Research output: Contribution to journalArticle

Baati, Rachid ; Barma, D. K. ; Falck, J R ; Mioskowski, Charles. / Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation-aldehyde addition. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 12. pp. 2179-2181.
@article{c9967f830b374acb89768696843e630d,
title = "Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation-aldehyde addition",
abstract = "Cr(II)-induced condensation of CCl4 or CBr4 with an aldehyde stereospecifically generates an (E)-α-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.",
keywords = "Alcohols, Alkenylation, Chromium, Stereocontrol, Vinylation",
author = "Rachid Baati and Barma, {D. K.} and Falck, {J R} and Charles Mioskowski",
year = "2002",
month = "3",
day = "18",
doi = "10.1016/S0040-4039(02)00206-X",
language = "English (US)",
volume = "43",
pages = "2179--2181",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation-aldehyde addition

AU - Baati, Rachid

AU - Barma, D. K.

AU - Falck, J R

AU - Mioskowski, Charles

PY - 2002/3/18

Y1 - 2002/3/18

N2 - Cr(II)-induced condensation of CCl4 or CBr4 with an aldehyde stereospecifically generates an (E)-α-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.

AB - Cr(II)-induced condensation of CCl4 or CBr4 with an aldehyde stereospecifically generates an (E)-α-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.

KW - Alcohols

KW - Alkenylation

KW - Chromium

KW - Stereocontrol

KW - Vinylation

UR - http://www.scopus.com/inward/record.url?scp=0037128469&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037128469&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)00206-X

DO - 10.1016/S0040-4039(02)00206-X

M3 - Article

VL - 43

SP - 2179

EP - 2181

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 12

ER -