Highly Enantioselective Construction of Multifunctional Silicon‐Stereogenic Silacycles by Asymmetric Enamine Catalysis

• Published in: Angewandte Chemie International Edition Vol. 62; no. 9; pp. e202217724 - n/a
• Main Authors: Zhang, Xue‐Xin, Gao, Yang, Zhang, Yan‐Xue, Zhou, Jian, Yu, Jin‐Sheng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 20.02.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Adducts; Asymmetric Enamine Catalysis; Asymmetry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Desymmetric Adolization; Enantiomers; Fluoroalkyl; Physical Sciences; Science & Technology; Silacycles; Silicon; Silicon compounds; Silicon-Stereocenter; ORGANIC CATALYSIS; ORGANOCATALYSIS; DESYMMETRIZATION; STRATEGIES; MOLECULES; Fluoroalkyl; AMINO-ACID; Desymmetric Adolization; Silicon-Stereocenter; CHEMISTRY; FLUORINE; Asymmetric Enamine Catalysis; Silacycles; DERIVATIVES; DIRECT ALDOL REACTIONS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202217724

We report the first highly enantioselective construction of silicon‐stereocenters by asymmetric enamine catalysis. An unprecedented desymmetric intramolecular aldolization of prochiral siladials was thus developed for the facile access of multifunctional silicon‐stereogenic silacycles in high to excellent enantioselectivity. With an enal moiety, these adducts could be readily elaborated for the diverse synthesis of silicon‐stereogenic compounds, and for late‐stage modification. The enantioselective construction of silicon‐stereocenter by asymmetric enamine catalysis is reported. The reaction proceeds via an unprecedented desymmetric intramolecular aldolization of prochiral siladials for the diverse synthesis of multifunctional silicon‐stereogenic silacycles.