Tetrahedron

Synthese stereoselective d'esters α, β-ethyleniques α-methyles Z ou E par la reaction de wittig-horner a partir de phosphonates ou d'oxydes de phosphine

G Etemad-Moghadam, J Seyden-Penne

Index: Etemad-Moghadam, Guita; Seyden-Penne, Jacqueline Tetrahedron, 1984 , vol. 40, # 24 p. 5153 - 5166

Full Text: HTML

Citation Number: 39

Abstract

The reaction of α-branched aldehydes with diethyl 1-carbomethoxyethyl phosphonate 1b in THF/nBuLi at low temperature leads stereoselectively to Z α-methyl α, β-unsaturated esters. From a linear aldehyde, the reaction is less stereoselective, while from α, β-unsaturated ones, the E isomers are predominantly formed in good yields. From diphenyl 1- carbomethoxyethyl phosphine oxide 2b, E α-methyl α, β-unsaturated esters are ...

Related Articles:

A Selective Ru??Catalyzed Semireduction of Alkynes to Z Olefins under Transfer??Hydrogenation Conditions

[Belger, Christian; Neisius, N. Matthias; Plietker, Bernd Chemistry - A European Journal, 2010 , vol. 16, # 40 p. 12214 - 12220]

Heck reaction catalyzed by Pd-modified zeolites

[Djakovitch; Koehler Journal of the American Chemical Society, 2001 , vol. 123, # 25 p. 5990 - 5999]

Catalyzed insertion reactions of substituted α-diazoesters. A new synthesis of cis-enoates

[Ikota, Nobuo; Takamura, Norio; Young, Stanley D.; Ganem, Bruce Tetrahedron Letters, 1981 , vol. 22, # 42 p. 4163 - 4166]

A convenient one-pot PCC oxidation-wittig reaction of alcohols

[Bressette, Andrew R.; Glover IV, Louis C. Synlett, 2004 , # 4 p. 738 - 740]

Lewis acid catalysis of photochemical reactions. 4. Selective isomerization of cinnamic esters

[Lewis, Frederick D.; Oxman, Joe D.; Gibson, Lester L.; Hampsch, Hilary L.; Quillen, Suzanne L. Journal of the American Chemical Society, 1986 , vol. 108, # 11 p. 3005 - 3015]

More Articles...