Asymmetric retro-[1,4] brook rearrangement and its stereochemical course at silicon

Atsuo Nakazaki; Takeshi Nakai; Katsuhiko Tomooka

doi:10.1002/anie.200503734

Asymmetric retro-[1,4] brook rearrangement and its stereochemical course at silicon

Atsuo Nakazaki, Takeshi Nakai, Katsuhiko Tomooka

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) Taking the silyl group a step further: An unprecedented rearrangement in an anion derived from an allyloxysilane occurs by a [1,4] shift of the silyl group (see scheme). The asymmetric synthesis of enantiomerically enriched γ-functionalized allylsilanes with Si stereocenters can be accomplished with this retro-[1,4] Brook rearrangement. E = electrophile.

Original language	English
Pages (from-to)	2235-2238
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	14
DOIs	https://doi.org/10.1002/anie.200503734
Publication status	Published - Mar 27 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.200503734

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AU - Nakai, Takeshi

AU - Tomooka, Katsuhiko

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AB - (Chemical Equation Presented) Taking the silyl group a step further: An unprecedented rearrangement in an anion derived from an allyloxysilane occurs by a [1,4] shift of the silyl group (see scheme). The asymmetric synthesis of enantiomerically enriched γ-functionalized allylsilanes with Si stereocenters can be accomplished with this retro-[1,4] Brook rearrangement. E = electrophile.

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Asymmetric retro-[1,4] brook rearrangement and its stereochemical course at silicon

Abstract

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