Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

Rachid Baati; Charles Mioskowski; Dhurke Kashinath; Sanjeevarao Kodepelly; Biao Lu; J. R. Falck

doi:10.1016/j.tetlet.2008.11.027

Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

Rachid Baati, Charles Mioskowski, Dhurke Kashinath, Sanjeevarao Kodepelly, Biao Lu, J. R. Falck

Biochemistry

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

9 Scopus citations

Abstract

Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl₂ under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.

Original language	English (US)
Pages (from-to)	402-405
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.027
State	Published - Jan 28 2009

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.11.027

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title = "Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes",

abstract = "Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.",

author = "Rachid Baati and Charles Mioskowski and Dhurke Kashinath and Sanjeevarao Kodepelly and Biao Lu and Falck, {J. R.}",

note = "Funding Information: We thank the CNRS, the ANR (DK and SK fellowships), the Robert A. Welch Foundation, and NIH (GM31278, DK38226) for financial support.",

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T1 - Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

AU - Baati, Rachid

AU - Mioskowski, Charles

AU - Kashinath, Dhurke

AU - Kodepelly, Sanjeevarao

AU - Lu, Biao

AU - Falck, J. R.

N1 - Funding Information: We thank the CNRS, the ANR (DK and SK fellowships), the Robert A. Welch Foundation, and NIH (GM31278, DK38226) for financial support.

PY - 2009/1/28

Y1 - 2009/1/28

N2 - Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.

AB - Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.

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Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

Abstract

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