Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles by Enantioselective [2+2+2] Cycloaddition

被引：100

作者：

Shintani, Ryo ^{[1
]}

Takagi, Chihiro ^{[1
]}

Ito, Tomoaki ^{[2
]}

Naito, Masanobu ^{[3
]}

Nozaki, Kyoko ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan

[2] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

[3] Natl Inst Mat Sci, Tsukuba, Ibaraki 3050044, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 05期

关键词：

asymmetric catalysis; cycloaddition; dibenzosilole; rhodium; silicon; CIRCULARLY-POLARIZED LUMINESCENCE; PI-CONJUGATED MOLECULES; SOLAR-CELLS; SPIROSILABIFLUORENE DERIVATIVES; PHOTOPHYSICAL PROPERTIES; PHOTOVOLTAIC PROPERTIES; ORGANOSILICON COMPOUNDS; ORGANIC ELECTRONICS; KINETIC RESOLUTION; POLYMERS;

D O I：

10.1002/anie.201409733

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzosiloles has been developed through a [2+2+2] cycloaddition of silicon-containing prochiral triynes with internal alkynes. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and the present catalysis is also applicable to the asymmetric synthesis of a germanium-stereogenic dibenzogermole. Preliminary studies on the optical properties of these compounds are also described.

引用

页码：1616 / 1620

页数：5

共 109 条

[1] Donor-acceptor dyes incorporating a stable dibenzosilole π-conjugated spacer for dye-sensitized solar cells [J].