Premium
Selective Synthesis of Silacycles by Borane‐Catalyzed Domino Hydrosilylation of Proximal Unsaturated Bonds: Tunable Approach to 1,n‐Diols
Author(s) -
Shin Kwangmin,
Joung Seewon,
Kim Youyoung,
Chang Sukbok
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700698
Subject(s) - hydrosilylation , chemistry , stereocenter , domino , borane , reagent , catalysis , selectivity , intramolecular force , combinatorial chemistry , organic chemistry , medicinal chemistry , enantioselective synthesis
The tris(pentafluorophenyl)boron‐catalyzed domino hydrosilylation of substrates carrying unsaturated functionalities in a proximal arrangement is presented to produce silacycles. Excellent levels of efficiency and selectivity were achieved in the cyclization by the deliberate choice of the hydrosilane reagents. The key to successful cyclic hydrosilylation is the reactivity enhancement of the second intramolecular hydrosilylation by a proximity effect. Not only dienes but also enones, enynes, ynones and enimines readily afford medium‐sized silacycles under convenient and mild conditions. The cyclization proceeds with acceptable diastereoselectivity mainly controlled by the conformational bias towards inducing additional stereogenic centers. The silacycles obtained from this reaction were converted to 1,n‐diols or 1,n‐amino alcohols upon oxidation, thus rendering the present cyclization a powerful tool for accessing synthetically valuable building blocks.