Enantioselective Multicomponent Reaction for Rapid Construction of 1,2,5-Triol Derivatives with Vicinal Chiral
Mingfeng Li1, Xin Guo1, Qing Zheng1
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , Shanghai 200062, China.
Abstract:
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.
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