Organocatalytic β,γ-Selective Activation of Deconjugated Butenolides Access to Chiral Tricyclic Chroman-butyrolactones

Yangqing Zheng; Weichao Jiang; Jingbo Tan; Juzhang Yan; Ruoting Zhan; Huicai Huang

doi:10.1021/acs.joc.1c01449

Organocatalytic β,γ-Selective Activation of Deconjugated Butenolides Access to Chiral Tricyclic Chroman-butyrolactones

J Org Chem. 2021 Sep 17;86(18):12821-12830. doi: 10.1021/acs.joc.1c01449. Epub 2021 Sep 1.

Authors

Yangqing Zheng¹, Weichao Jiang¹, Jingbo Tan¹, Juzhang Yan¹, Ruoting Zhan¹, Huicai Huang^{1

2}

Affiliations

¹ Key Laboratory of Chinese Medicinal Resource from Lingnan, Ministry of Education, School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, P.R. China.
² Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, P.R. China.

PMID: 34465087
DOI: 10.1021/acs.joc.1c01449

Abstract

A highly efficient method for the β,γ-selective activation of deconjugated butenolides has been developed through an organocatalytic asymmetric vinylogous cascade reaction. This protocol enables the construction of a broad range of substituted tricyclic chroman-butyrolactones by vinylogous Michael/oxa-Michael pathways in good yield (up to 89%) with good to high enantioselectivity (up to 97:3 er) and excellent diastereoselectivity. The ring-opening esterification of butyrolactones was also demonstrated.