Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures

Autor:	Giorgiana Denisa Bisag, Pietro Pecchini, Michele Mancinelli, Mariafrancesca Fochi, Luca Bernardi
Přispěvatelé:	Bisag, Giorgiana Denisa, Pecchini, Pietro, Mancinelli, Michele, Fochi, Mariafrancesca, Bernardi, Luca
Rok vydání:	2022
Předmět:	Cyclopropanes Organic Chemistry Benzopyrans Stereoisomerism Chroman Chromans Physical and Theoretical Chemistry Biochemistry Benzopyran
Zdroj:	Organic Letters. 24:5468-5473
ISSN:	1523-7052 1523-7060
Popis:	The 1,1a,2,7b-tetrahydrocyclopropa[c]chromene, aris-ing from fusion of chromane and cyclopropane rings is the core of medicinally relevant compounds. Engaging sulfoxonium ylides in enantioselective aminocatalytic reactions for the first time, a convenient entry to this scaffold is presented. Several ring-fused derivatives were obtained in moderate-to-good yields and enantiose-lectivities and with perfect diastereoselectivity at the cyclopropane, using an alpha,alpha-diphenylprolinol aminocatalyst. The versatility of the hemiacetal moiety in the products was leveraged to effect various synthetic manipulations.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::da8b579542e2523c4689db49c0be6c33 https://doi.org/10.1021/acs.orglett.2c02204 Zobrazit plný text záznamu