An asymmetric allylic alkylation-Smiles rearrangement-sulfinate addition sequence to construct chiral cyclic sulfones.

Wang, Quan-Gang; Zhou, Qing-Qing; Deng, Jin-Gen; Chen, Ying-Chun

Wang, Quan-Gang; Zhou, Qing-Qing; Deng, Jin-Gen; Chen, Ying-Chun.

Afiliación

Wang QG; Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, Sichuan 610041, China, and College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.

Org Lett ; 15(18): 4786-9, 2013 Sep 20.

Article en En | MEDLINE | ID: mdl-23992537

ABSTRACT

ABSTRACT

An asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates and ß-keto sulfones was investigated by the catalysis of modified cinchona alkaloids, whose products underwent a Smiles rearrangement-sulfinate addition cascade to furnish highly functionalized five-membered cyclic sulfones in moderate to excellent enantioselectivity and good diastereoselectivity after treatment with DBU.

Asunto(s)

Compuestos Alílicos/química; Carbonatos/química; Alcaloides de Cinchona/química; Sulfonas/síntesis química; Alquilación; Catálisis; Estructura Molecular; Estereoisomerismo; Sulfonas/química

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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Sulfonas / Carbonatos / Alcaloides de Cinchona / Compuestos Alílicos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2013 Tipo del documento: Article País de afiliación: China

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