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

Tetrahedron Letters

Volumn 50, Issue 4, 2009, Pages 402-405

  Baati, Rachid ^a   Mioskowski, Charles ^a   Kashinath, Dhurke ^a   Kodepelly, Sanjeevarao ^a   Lu, Biao ^b   Falck, J R ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; CARBENOID; CARBON; CHROMIUM; VINYLIDENE CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REFORMATSKY REACTION; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 57149140849     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.027     Document Type: Article

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31. 1H NMR of the crude reaction mixture. The stereochemistry of the major Z acrylate was assigned by NOE experiments.
32. 3) δ 53.3, 55.7, 61.1, 114.6, 119.7, 127.2, 128.9, 129.8, 137.8, 144.5, 160.5, 164.9.
33. The use of other solvents, under otherwise identical conditions, was not satisfactory: EtOAc, benzene, and dioxane afforded 3 in 18%, 5%, and 38% yield, respectively.