Synlett 2018; 29(04): 388-396
DOI: 10.1055/s-0036-1591839
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© Georg Thieme Verlag Stuttgart · New York

Recent Progress in Catalytic Enantioselective Desymmetrization of Prochiral Organosilanes for the Synthesis of Silicon-Stereogenic Compounds

Ryo Shintani*
Division of Chemistry, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan   eMail: [email protected]
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Support has been provided in part by a Grant-in-Aid for Scientific Research (B) (16H04145) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
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Publikationsverlauf

Received: 29. September 2017

Accepted after revision: 27. Oktober 2017

Publikationsdatum:
23. November 2017 (online)


Abstract

It is highly important to develop efficient synthetic methods for various enantioenriched chiral compounds due to their high significance in our life. In this regard, asymmetric catalysis is one of the most attractive ways of synthesizing such compounds from achiral precursors. Although various methods have been developed for the enantio­selective preparation of carbon-stereogenic compounds, the corresponding methods for silicon-stereogenic compounds are much less established. In particular, little progress has been made on catalytic enantioselective synthesis using prochiral organosilanes until recently. This account focuses on the recent progress in the catalytic enantio­selective preparation of silicon-stereogenic organosilanes through ­desymmetrization of prochiral organosilanes.

1 Introduction

2 Desymmetrization of Diorganodihydrosilanes

3 Desymmetrization of Tetraorganosilanes

3.1 Desymmetrization through Cleavage of Silicon–Carbon Bonds

3.2 Desymmetrization without Cleavage of Silicon–Carbon Bonds

4 Conclusion

 
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