Effects of Silyl Substituents on the Palladium??Catalyzed Asymmetric Synthesis of Axially Chiral (Allenylmethyl) silanes and Their SE2′ Chirality Transfer Reactions

M Ogasawara, Y Ge, A Okada…

文献索引：Ogasawara, Masamichi; Ge, Yonghui; Okada, Atsushi; Takahashi, Tamotsu European Journal of Organic Chemistry, 2012 , # 8 p. 1656 - 1663

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被引用次数: 8

摘要

Abstract A series of axially chiral 4-substituted-1-silyl-2, 3-butadienes [(allenylmethyl) silanes] were synthesized from 3-bromo-5-silylpenta-1, 3-dienes by a Pd-catalyzed asymmetric reaction with a soft nucleophile. The optically active (allenylmethyl) silanes react with an acetal in the presence of TiCl 4 to give the enantiomerically enriched 1, 3-diene derivatives through an SE 2′ pathway. Effects of the silyl groups on the enantioselectivity ...