Synthetic communications

Practical Stereoselective Synthesis of (2 E)??and (2 Z)??4??Cycloalkylidenebut??2??enoic Acids

SK Karagiozov, FS Abbott

Index: Karagiozov, Stoyan K.; Abbott, Frank S. Synthetic Communications, 2004 , vol. 34, # 5 p. 871 - 888

Full Text: HTML

Citation Number: 3

Abstract

Abstract Stereoselective synthesis of α, β??unsaturated esters 7 and 8 was achieved through Horner–Wadsworth–Emmons reaction of β, β??disubstituted α, β??unsaturated aldehydes. Thus, aldehydes 6 undergo olefination with phosphonate carbanion generated from triethyl phosphonoacetate 3 and lithium hydroxide or butyl lithium/DMPU to give (E)?螃?, β?? unsaturated esters 7 with excellent selectivity. The treatment of 6 with the new Horner– ...

Related Articles:

Dienamines as Diels-Alder dienes. An efficient cyclohexannulation sequence

[Snowden, Roger L.; Wuest, Manfred Tetrahedron Letters, 1986 , vol. 27, # 6 p. 699 - 702]

Dienamines as Diels-Alder dienes. An efficient cyclohexannulation sequence

[Snowden, Roger L.; Wuest, Manfred Tetrahedron Letters, 1986 , vol. 27, # 6 p. 699 - 702]

Dilithiated 3-tosylpropanal dimethyl acetal as β, β-acylvinyl dianion or homoenolate dianion equivalent

[Bonete, Pedro; Najera, Carmen Tetrahedron, 1996 , vol. 52, # 11 p. 4111 - 4122]

Aldehydes from dihydro-1, 3-oxazines. II. Synthesis of. alpha.,. beta.-unsaturated aldehydes and their C-1 deuterated derivatives

[Meyers,A.I. et al. Journal of the American Chemical Society, 1969 , vol. 91, p. 764 - 765]

Synthesis of aldehydes from dihydro-1, 3-oxazines

[Meyers,A.I. et al. Journal of Organic Chemistry, 1973 , vol. 38, p. 36 - 56]

More Articles...