Tetrahedron

Reaction of acylsilanes with sulfur ylides. selective formation of silyl enol ethers or β-ketosilanes.

T Nakajima, M Segi, F Sugimoto, R Hioki, S Yokota…

Index: Nakajima, Tadashi; Segi, Masahito; Sugimoto, Fumitosi; Hioki, Reiko; Yokota, Seiko; Miyashita, Kiyoshi Tetrahedron, 1993 , vol. 49, # 37 p. 8343 - 8358

Full Text: HTML

Citation Number: 28

Abstract

The reaction of acylsilanes with sulfur ylides in THF results in the formation of the corresponding silyl enol ethers or β-ketosilanes. The relative ratio of these products varies with the ylide conditions and the stability of ylide used. It is noteworthy that silyl enol ethers were formed under the salt-free ylide conditions, and that β-ketosilanes were yielded in the presence of soluble inorganic salts in THF, selectively. The formation of both products ...

Related Articles:

Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

[Fuerstner, Alois; Kollegger, Gerlinde; Weidmann, Hans Journal of Organometallic Chemistry, 1991 , vol. 414, # 3 p. 295 - 305]

Silafunctional compounds in organic synthesis: XVIII. Oxidative cleavage of the silicon-carbon bond in alkenylfluorosilanes to carbonyl compounds: Synthetic and …

[Tamao, Kohei; Akita, Munetaka; Kumada, Makoto Journal of Organometallic Chemistry, 1983 , vol. 254, # 1 p. 13 - 22]

… of ((4 R, 5 S)-5-Amino-4-(2, 4, 5-trifluorophenyl) cyclohex-1-enyl)-(3-(trifluoromethyl)-5, 6-dihydro-[1, 2, 4] triazolo [4, 3-a] pyrazin-7 (8 H)-yl) methanone (ABT-341), a …

[Pei, Zhonghua; Li, Xiaofeng; Von Geldern, Thomas W.; Madar, David J.; Longenecker, Kenton; Yong, Hong; Lubben, Thomas H.; Stewart, Kent D.; Zinker, Bradley A.; Backes, Bradley J.; Judd, Andrew S.; Mulhern, Mathew; Ballaron, Stephen J.; Stashko, Michael A.; Mika, Amanda K.; Beno, David W. A.; Reinhart, Glenn A.; Fryer, Ryan M.; Preusser, Lee C.; Kempf-Grote, Anita J.; Sham, Hing L.; Trevillyan, James M. Journal of Medicinal Chemistry, 2006 , vol. 49, # 22 p. 6439 - 6442]

Metal-catalyzed rearrangement of cyclopropenes to allenes

[Sun, Chunrui; Li, Jingwei; Demerzhan, Silviya; Lee, Daesung Arkivoc, 2011 , vol. 2011, # 4 p. 17 - 25]

. alpha.-Trimethylsilyl boronic esters. Pinacol lithio (trimethylsilyl) methaneboronate, homologation of boronic esters with [chloro (trimethylsilyl) methyl] lithium, and …

[Matteson, Donald S.; Majumdar, Debesh Organometallics, 1983 , vol. 2, p. 230 - 236]

More Articles...