Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Enantioselective Multicomponent Reaction for Rapid Construction of 1,2,5-Triol Derivatives with Vicinal Chiral Centers

Enantioselective Multicomponent Reaction for Rapid Construction of 1,2,5-Triol Derivatives with Vicinal Chiral Centers
Shunying Liu, Qing Zheng, Wenhao Hu, Xin Guo, Mingfeng Li
1,2,5-Triol derivatives with vicinal chiral centers have been synthesized from simple starting materials by one-pot method in good yields and with an excellent enantioselectivity. This process was promoted by a chiral secondary amine and iridium(I) cocatalyzed three-component reaction of aryldiazoacetates and alcohols with enals as electrophiles followed by a reduction with NaBH4. Iridium(I)-associated oxonium ylide intermediates were efficiently generated and successfully trapped by the amine-activated enals via a selective 1,4-addition manner, generating enantioselective three-component coupling products.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00473

DOI: 10.1021/acs.joc.7b00473

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