Tetrahedron letters

Highly selective γ-alkylation of triisopropylsilylallyl anion. Synthesis of α-triisopropylsilyl aldehydes.

JM Muchowski, R Naef, ML Maddox

Index: Muchowski, Joseph M.; Naef, Reto; Maddox, Michael L. Tetrahedron Letters, 1985 , vol. 26, # 44 p. 5375 - 5378

Full Text: HTML

Citation Number: 40

Abstract

Abstract The reaction of triisopropylsilylallyllithium with alkyl halides took place with considerably greater γ-selectivity than reported for trimethylsilyl allyllithium. Silica gel induced rearrangement of the epoxides 5 derived from the alkylation products 3 gave α- triisopropylsilyl aldehydes 6 by a process in which silyl group transposition occurred with predominant inversion at the migration terminus.

~95%

Zinc-catalyzed nucleophilic substitution reaction of chloros...

[Murakami, Kei; Yorimitsu, Hideki; Oshima, Koichiro Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1415 - 1417]

Rhodium (II)-Catalyzed Stereoselective Synthesis of Allylsil...

[Guptill, David M.; Cohen, Carolyn M.; Davies, Huw M. L. Organic Letters, 2013 , vol. 15, # 24 p. 6120 - 6123]

Kinetics of the reactions of allylsilanes, allylgermanes, an...

[Hagen, Gisela; Mayr, Herbert Journal of the American Chemical Society, 1991 , vol. 113, # 13 p. 4954 - 4961]

Copper-catalyzed arylation of chlorosilanes with Grignard re...

[Morita, Eiji; Murakami, Kei; Iwasaki, Masayuki; Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro Bulletin of the Chemical Society of Japan, 2009 , vol. 82, # 8 p. 1012 - 1014]