Silicon‐Stereogenic Monohydrosilane: Synthesis and Applications

• Published in: Angewandte Chemie International Edition Vol. 61; no. 36; pp. e202205382 - n/a
• Main Authors: Wu, Yichen, Wang, Peng
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 05.09.2022
• Edition: International ed. in English
• Subjects: Asymmetric Catalysis; Asymmetric synthesis; Chemical synthesis; Chirality; Hydrogen bonds; Monohydrosilanes; Optical activity; Optoelectronics; Organic chemistry; Reagents; Silicon; Silylation; Transition Metals; asymmetric catalysis, chirality, monohydrosilane, silylation, transition metal
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.202205382

Optically active organosilanes have been demonstrated to be versatile chiral reagents in synthetic chemistry since the early seminal contributions by Sommer and Corriu. Among these silicon‐containing chiral architectures, monohydrosilanes, which bear a Si−H bond, hold a unique position because of their facile transformations through stereospecific Si–carbon or Si–heteroatom bond‐formation reactions. In addition, those compounds have also been leveraged as chiral reagents for alcohol resolution, chiral auxiliaries, mechanistic probes, as well as potential optoelectronic materials. This Minireview comprehensively summarizes the synthesis and synthetic applications of silicon‐stereogenic monohydrosilanes, particularly the advances in the transition‐metal‐catalyzed asymmetric synthesis of this class of functional molecules. Monohydrosilanes, which bear a Si−H bond, have been widely leveraged as chiral reagents for alcohol resolution, chiral auxiliaries, mechanistic probes, as well as potential optoelectronic materials. This Minireview comprehensively summarizes the synthesis and synthetic applications of silicon‐stereogenic monohydrosilanes, particularly the advances in transition‐metal‐catalyzed asymmetric synthesis.