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1‐Silyl‐1‐boryl‐2‐alkenes: Reagents for Stereodivergent Allylation Leading to 4‐Oxy‐( E )‐1‐alkenylboronates and 4‐Oxy‐( Z )‐1‐alkenylsilanes
Author(s) -
Shimizu Masaki,
Kitagawa Hirotaka,
Kurahashi Takuya,
Hiyama Tamejiro
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011119)40:22<4283::aid-anie4283>3.0.co;2-3
Subject(s) - lithium diisopropylamide , silylation , chemistry , reagent , borane , lewis acids and bases , lithium (medication) , ketene , boranes , organic chemistry , organic synthesis , medicinal chemistry , catalysis , boron , medicine , ion , deprotonation , endocrinology
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.