(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

D. K. Barma; Abhijit Kundu; Hongming Zhang; Charles Mioskowski; J R Falck

doi:10.1021/ja029938d

(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

D. K. Barma, Abhijit Kundu, Hongming Zhang, Charles Mioskowski, J R Falck

Biochemistry

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

77 Scopus citations

Abstract

(Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 °C.

Original language	English (US)
Pages (from-to)	3218-3219
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	11
DOIs	https://doi.org/10.1021/ja029938d
State	Published - Mar 19 2003

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "(Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 °C.",

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year = "2003",

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T1 - (Z)-α-haloacrylates

T2 - An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

AU - Barma, D. K.

AU - Kundu, Abhijit

AU - Zhang, Hongming

AU - Mioskowski, Charles

AU - Falck, J R

PY - 2003/3/19

Y1 - 2003/3/19

N2 - (Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 °C.

AB - (Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 °C.

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(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

Abstract

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