Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide

Keisuke Yoshida; Hina Suzuki; Hiroki Inoue; Kohei Matsui; Yuta Fujino; Yohei Kanoko; Yukihiro Itatsu; Ken Ichi Takao

doi:10.1002/adsc.201600209

Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide

Keisuke Yoshida, Hina Suzuki, Hiroki Inoue, Kohei Matsui, Yuta Fujino, Yohei Kanoko, Yukihiro Itatsu, Ken Ichi Takao

Department of Applied Chemistry

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

8 Citations (Scopus)

Abstract

The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as (tert-butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph₃SiCl) was developed. The reaction was effectively catalyzed with 4-methoxypyridine N-oxide in the presence of sodium sulfate (Na₂SO₄). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol. (Figure presented.) .

Original language	English
Pages (from-to)	1886-1891
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	12
DOIs	https://doi.org/10.1002/adsc.201600209
Publication status	Published - 2016 Jun 16

Keywords

amine N-oxides
organocatalysis
regioselectivity
silicon

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201600209

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title = "Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide",

abstract = "The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as (tert-butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph3SiCl) was developed. The reaction was effectively catalyzed with 4-methoxypyridine N-oxide in the presence of sodium sulfate (Na2SO4). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol. (Figure presented.) .",

keywords = "amine N-oxides, organocatalysis, regioselectivity, silicon",

author = "Keisuke Yoshida and Hina Suzuki and Hiroki Inoue and Kohei Matsui and Yuta Fujino and Yohei Kanoko and Yukihiro Itatsu and Takao, {Ken Ichi}",

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T1 - Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives

T2 - Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide

AU - Yoshida, Keisuke

AU - Suzuki, Hina

AU - Inoue, Hiroki

AU - Matsui, Kohei

AU - Fujino, Yuta

AU - Kanoko, Yohei

AU - Itatsu, Yukihiro

AU - Takao, Ken Ichi

PY - 2016/6/16

Y1 - 2016/6/16

N2 - The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as (tert-butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph3SiCl) was developed. The reaction was effectively catalyzed with 4-methoxypyridine N-oxide in the presence of sodium sulfate (Na2SO4). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol. (Figure presented.) .

AB - The highly regioselective organocatalytic chlorosilylation of oxirane derivatives using bulky silyl reagents such as (tert-butyl)diphenylsilyl chloride (TBDPSCl) or triphenylsilyl chloride (Ph3SiCl) was developed. The reaction was effectively catalyzed with 4-methoxypyridine N-oxide in the presence of sodium sulfate (Na2SO4). Several silylated halohydrins were obtained with complete regioselectivity and the reaction was applied to the synthesis of carvedilol. (Figure presented.) .

KW - amine N-oxides

KW - organocatalysis

KW - regioselectivity

KW - silicon

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Organocatalytic Regioselective Chlorosilylation of Oxirane Derivatives: Mild and Effective Insertion of Bulky Silyl Chloride by Using 4-Methoxypyridine N-Oxide

Abstract

Keywords

ASJC Scopus subject areas

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