Synthesis of a Chiral Borate Counteranion, Its Trityl Salt, and Application Thereof in Lewis‐Acid Catalysis

Autor:	Martin Oestreich, Phillip Pommerening, Jens Mohr, Jonas Friebel
Rok vydání:	2017
Předmět:	chemistry.chemical_classification Mukaiyama aldol addition 010405 organic chemistry Chemistry Hydride Organic Chemistry Cationic polymerization Salt (chemistry) 010402 general chemistry 01 natural sciences Asymmetric induction 0104 chemical sciences Lewis acid catalysis Catalysis Polymer chemistry Electrophile Organic chemistry Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2017:2312-2316
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.201700239
Popis:	The preparation of a chiral derivative of [B(C6F5)4]– in which the fluorine atom in the para position of each of the C6F5 groups is replaced by a 1,1′-binaphthalen-2-yl group is described. The new counteranion was isolated as its lithium, sodium, and trityl salts. The chiral trityl salt was then used as a catalyst in selected counteranion-directed Diels–Alder reactions and a Mukaiyama aldol addition, but no asymmetric induction was achieved. Application of the chiral trityl salt to the generation of silicon cations by silicon-to-carbon hydride transfer from hydrosilanes failed, presumably as a result of the incompatibility of the relatively electron-rich naphthyl groups in the borate and the cationic silicon electrophiles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::33cf7ee619d02bf4268c00228975d4c7 https://doi.org/10.1002/ejoc.201700239 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.