Synthesis and applications of chiral organoboranes generated from sulfonium ylides

VK Aggarwal, GY Fang, AT Schmidt

Index: Aggarwal, Varinder K.; Guang, Yu Fang; Schmidt, Andreas T. Journal of the American Chemical Society, 2005 , vol. 127, # 6 p. 1642 - 1643

Full Text: HTML

Citation Number: 47

Abstract

The reactions of aryl-stabilized sulfonium ylides with trialkyl/triarylboranes have been investigated. Clean monohomologation of the boranes with only a small amount of the higher homologation products (< 10%) was observed. The homologation products were isolated as the alcohols (treatment with H2O2/NaOH) and amines (treatment with NH2OSO3H). Although the reactions were conveniently conducted at 5° C, the ylide ...

Related Articles:

Asymmetric alkylation of N-toluenesulfonylimines with dialkylzinc reagents catalyzed by copper-chiral amidophosphine

[Itsuno, Shinichi; Yanaka, Hiromitsu; Hachisuka, Chiharu; Ito, Koichi Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 5 p. 1341 - 1342]

Carbon–carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

[Niwa, Takashi; Suehiro, Takafumi; Yorimitsu, Hideki; Oshima, Koichiro Tetrahedron, 2009 , vol. 65, # 26 p. 5125 - 5131]

A new synthesis of primary amines from diarylidenesulfamides

[Davis, Franklin A.; Giangiordano, Mark A.; Starner, William E. Tetrahedron Letters, 1986 , vol. 27, # 34 p. 3957 - 3960]

Reaction of aldehyde O-alkyl oxime with organometallic compounds

[Itsuno, Shinichi; Miyazaki, Koji; Ito, Koichi Tetrahedron Letters, 1986 , vol. 27, # 26 p. 3033 - 3036]

Synthesis and Configurational Assignment of the Amino Alcohol in the Eastern Fragment of the GE2270 Antibiotics by Regio-and Stereoselective Addition of 2- …

[Hirao, Akira; Hattori, Iwakazu; Yamaguchi, Kazuo; Nakahama, Seiichi; Yamazaki, Noboru Synthesis, 1982 , # 6 p. 461 - 462]

More Articles...