Synthesis of. alpha.-ketols mediated by divalent samarium compounds

J Collin, JL Namy, F Dallemer…

Index: Collin, Jacqueline; Namy, Jean-Louis; Dallemer, Frederic; Kagan, Henri B. Journal of Organic Chemistry, 1991 , vol. 56, # 9 p. 3118 - 3122

Full Text: HTML

Citation Number: 70

Abstract

Coupling reactions of acid chlorides are mediated by SmI, and SmCp,, leading to a-ketols 3. Condensation reactions of acid chlorides on aldehydes similarly product a-ketols 5; with ketones, best results are obtained with use of SmIP Reactivities of SmIz and SmCp, are compared and mechanisms of the reactions discussed. Formation of an acylsamarium species is shown.

~63%

~11%

~85%

~63%

Imidoyl chlorides as starting materials for the preparation ...

[Alonso, Emma; Ramon, Diego J.; Yus, Miguel Tetrahedron, 1998 , vol. 54, # 39 p. 12007 - 12028]

Synthesis of. alpha.-hydroxy ketones by direct, low-temperat...

[Seyferth, Dietmar; Weinstein, Robert M.; Hui, Richard C.; Wang, Wei-Liang; Archer, Colin M. Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5620 - 5629]

Properties of. alpha.-keto cations. Facile generation under ...

[Creary,X.; Geiger,C.C. Journal of the American Chemical Society, 1982 , vol. 104, p. 4151]