Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

Autor:	Gregory R. Boyce, Stefania F. Musolino, Jianing Yang, Andrew D. Smith, James E. Taylor
Přispěvatelé:	EPSRC, The Leverhulme Trust, University of St Andrews. School of Chemistry
Rok vydání:	2022
Předmět:	Organic Chemistry DAS QD QD Chemistry
Zdroj:	The Journal of Organic Chemistry. 87:13367-13374
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.2c01602
Popis:	Funding: Florida Gulf Coast University; University of St Andrews; UK Engineering and Physical Sciences Research Council - EP/J018139/1, EP/L016419/1, EP/V051423/1; Leverhulme Trust - ECF-2014-005. The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate. Publisher PDF
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9d61efcaa5dae33302256953d8fd7e66 https://doi.org/10.1021/acs.joc.2c01602 Zobrazit plný text záznamu