α-Oxoketene dithioacetals: Versatile substrates for 1, 3-carbonyl transpositions
RK Dieter, Y Jenkitkasemwong
Index: Dieter, R. Karl; Jenkitkasemwong, Yawares Tetrahedron Letters, 1982 , vol. 23, # 37 p. 3747 - 3750
Full Text: HTML
Citation Number: 14
Abstract
Abstract A two step procedure for the conversion of α-oxoketene dithioacetals to β- substituted α, β-unsaturated thioesters or acids is described. The overall transformation represents a 1, 3-carbonyl transposition in which the original ketone carbonyl emerges as the carbonyl of an acid or thioester. The resulting thioesters and acids constitute versatile acylating reagents in accord with established procedures.
Related Articles:
[Bouillon, Jean-Philippe; Portella, Charles; Bouquant, James; Humbel, Stephane Journal of Organic Chemistry, 2000 , vol. 65, # 18 p. 5823 - 5830]
Iridium complex-catalyzed addition of water and alcohols to non-activated terminal alkynes
[Hirabayashi, Tomotaka; Okimoto, Yoshio; Saito, Akiyo; Morita, Masao; Sakaguchi, Satoshi; Ishii, Yasutaka Tetrahedron, 2006 , vol. 62, # 10 p. 2231 - 2234]
Efficient synthesis of 2-methyl-1-cyclopentene-1-carboxylic acid
[Harding, Kenn E.; Clement, Katherine S.; Gilbert, John C.; Wiechman, Barry Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2049 - 2050]
[Danheiser, Rick L.; Carini, David J.; Basak, Ajoy Journal of the American Chemical Society, 1981 , vol. 103, # 6 p. 1604 - 1606]
Hydration of alkynes in anhydrous medium with formic acid as water donor
[Menashe, Naim; Shvo, Youval Journal of Organic Chemistry, 1993 , vol. 58, # 26 p. 7434 - 7439]