Catalytic asymmetric coupling of vinylogous species via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. Issue 40 (20th April 2021)

• Record Type: Journal Article
• Authors: Yuan, Shu-Pei; Zhang, Xia-Yan; Jia, Yun-Qing; Wang, Zhen-Hua; Zhao, Jian-Qiang; You, Yong; Zhou, Ming-Qiang; Yuan, Wei-Cheng
• Is Part Of: Chemical communications. Volume 57:Issue 40(2021)
• Page Start: 4938
• Page End: 4941
• Publication Date: 2021-04-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc00777g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient catalytic asymmetric coupling of vinylogous species was developed for the synthesis of enantioenriched sec -alkyl-3-substituted indoles containing adjacent quaternary-tertiary stereocenters in synthetically viable results. Abstract : An efficient catalytic asymmetric coupling of vinylogous species is developed via deconjugated butenolide addition to vinylogous imines in situ generated from arylsulfonyl indoles. With quinine-derived bifunctional squaramide as the catalyst, a series of structurally diverse enantioenriched sec -alkyl-3-substituted indoles containing valuable γ, γ -disubstituted butenolide moieties and adjacent quaternary-tertiary stereocenters are obtained in synthetically viable results (up to 97% yield, 77 : 23 dr and 97% ee).