Silanes in organic synthesis. 21. Configurational stability of the 2, 2-diphenyl-1-(trimethylsilyl) cyclopropyl carbanion and free radical. Absolute stereochemical …

LA Paquette, T Uchida, JC Gallucci

文献索引：Paquette, Leo A.; Uchida, Takane; Gallucci, Judith C. Journal of the American Chemical Society, 1984 , vol. 106, # 2 p. 335 - 340

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被引用次数: 18

摘要

Abstract 2, 2-Diphenylcyclopropanecarboxylic acid was silylated at the 1-position and this product was resolved with/-cinchonidine. The resulting optically active acid was transformed into (-)-2, 2-diphenyl-1-methyl-1-(trimethylsilyl) cyclopropane, whose absolute configuration was shown to be R by metalation and silylation of (-)-(R)-6. The latter reaction proceeds with retention of configuration. In this way, the levorotatory form of (-)-3 was established to be R ...