1‐Silyl‐1‐boryl‐2‐alkenes: Reagents for Stereodivergent Allylation Leading to 4‐Oxy‐(E)‐1‐alkenylboronates and 4‐Oxy‐(Z)‐1‐alkenylsilanes

1‐Silyl‐1‐boryl‐2‐alkenes: Reagents for Stereodivergent Allylation Leading to 4‐Oxy‐(E)‐1‐alkenylboronates and 4‐Oxy‐(Z)‐1‐alkenylsilanes

Silylboryl reagents for organic synthesis: 1‐silyl‐1‐boryl‐2‐alkenes (2) were prepared efficiently by gem‐silylborylation of α‐chloroallyllithium compounds from (dimethylphenylsilyl)(pinacolato)borane (1; see scheme, LDA=lithium diisopropylamide) and were demonstrated to allylate acetals and aldehyd...

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Veröffentlicht in:Angewandte Chemie International Edition 2001-11, Vol.40 (22), p.4283-4286
Hauptverfasser: Shimizu, Masaki, Kitagawa, Hirotaka, Kurahashi, Takuya, Hiyama, Tamejiro
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alkenes
allylation
boron
carbenoids
silicon
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creator Shimizu, Masaki
Kitagawa, Hirotaka
Kurahashi, Takuya
Hiyama, Tamejiro
description Silylboryl reagents for organic synthesis: 1‐silyl‐1‐boryl‐2‐alkenes (2) were prepared efficiently by gem‐silylborylation of α‐chloroallyllithium compounds from (dimethylphenylsilyl)(pinacolato)borane (1; see scheme, LDA=lithium diisopropylamide) and were demonstrated to allylate acetals and aldehydes in the presence of a Lewis acid to produce (E)‐4‐alkoxy‐alkenylboronates. Heating the reagents with aldehydes in the absence of Lewis acid afforded (Z)‐4‐hydroxy‐alkenylsilanes stereospecifically.
doi_str_mv 10.1002/1521-3773(20011119)40:22<4283::AID-ANIE4283>3.0.CO;2-3
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source Wiley Online Library Journals Frontfile Complete
subjects alkenes
allylation
boron
carbenoids
silicon
title 1‐Silyl‐1‐boryl‐2‐alkenes: Reagents for Stereodivergent Allylation Leading to 4‐Oxy‐(E)‐1‐alkenylboronates and 4‐Oxy‐(Z)‐1‐alkenylsilanes
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