Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers

Autor:	Hui Zhou, Jung Tae Han, Nils Nöthling, Monika M. Lindner, Judith Jenniches, Clemens Kühn, Nobuya Tsuji, Li Zhang, Benjamin List
Rok vydání:	2022
Předmět:	Aromatic compounds Silicon Catalysts Inorganic compounds Stereoisomerism General Chemistry Biochemistry Catalysis Hydrocarbons Carbon Group 14 compounds Colloid and Surface Chemistry ddc:540 Ethers
Zdroj:	Journal of the American Chemical Society 144(23), 10156-10161 (2022). doi:10.1021/jacs.2c04261
ISSN:	1520-5126
DOI:	10.1021/jacs.2c04261
Popis:	Journal of the American Chemical Society 144(23), 10156 - 10161 (2022). doi:10.1021/jacs.2c04261 Functionalized enantiopure organosilanes are important building blocks with applications in various fields of chemistry; nevertheless, asymmetric synthetic methods for their preparation are rare. Here we report the first organocatalytic enantioselective synthesis of tertiary silyl ethers possessing “central chirality” on silicon. The reaction proceeds via a desymmetrizing carbon–carbon bond forming silicon–hydrogen exchange reaction of symmetrical bis(methallyl)silanes with phenols using newly developed imidodiphosphorimidate (IDPi) catalysts. A variety of enantiopure silyl ethers was obtained in high yields with good chemo- and enantioselectivities and could be readily derivatized to several useful chiral silicon compounds, leveraging the olefin functionality and the leaving group nature of the phenoxy substituent. Published by ACS Publications, Washington, DC
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f9254cddfe48e338ed256d0ac801a507 https://pubmed.ncbi.nlm.nih.gov/35649270 Zobrazit plný text záznamu