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.

Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures / Bisag, Giorgiana Denisa; Pecchini, Pietro; Mancinelli, Michele; Fochi, Mariafrancesca; Bernardi, Luca. - In: ORGANIC LETTERS. - ISSN 1523-7060. - ELETTRONICO. - 24:29(2022), pp. 5468-5473. [10.1021/acs.orglett.2c02204]

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

Bisag, Giorgiana Denisa;Pecchini, Pietro;Mancinelli, Michele;Fochi, Mariafrancesca
;
Bernardi, Luca
2022

Abstract

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.
2022
Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures / Bisag, Giorgiana Denisa; Pecchini, Pietro; Mancinelli, Michele; Fochi, Mariafrancesca; Bernardi, Luca. - In: ORGANIC LETTERS. - ISSN 1523-7060. - ELETTRONICO. - 24:29(2022), pp. 5468-5473. [10.1021/acs.orglett.2c02204]
Bisag, Giorgiana Denisa; Pecchini, Pietro; Mancinelli, Michele; Fochi, Mariafrancesca; Bernardi, Luca
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/898878
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