The catalytic asymmetric dearomatization of tryptamine for accessing meso-contiguous quaternary carbon centers of oligomeric cyclotryptamine alkaloids: a formal synthesis of hodgkinsine B. Issue 13 (22nd April 2021)

• Record Type: Journal Article
• Authors: Wei, Hongbo; Chen, Guzhou; Zou, Huanhuan; Zhou, Zhiqiang; Lei, Pan; Yan, Jiahang; Xie, Weiqing
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 13(2021)
• Page Start: 3255
• Page End: 3259
• Publication Date: 2021-04-22
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00393c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Herein, we disclosed a catalytic asymmetric dearomatization (CADA) of tryptamine via tandem [4 + 2] cycloaddition/cyclization with o -azaxylylene in situ generated from functionalized 3-bromooxindole promoted by chiral N, N ′-dioxide/Ni(BF4 )2 . Abstract : Herein, we disclosed a catalytic asymmetric dearomatization (CADA) of tryptamine via tandem [4 + 2] cycloaddition/cyclization with o -azaxylylene in situ generated from functionalized 3-bromooxindole promoted by chiral N, N ′-dioxide/Ni(BF4 )2 . A variety of dimeric tryptamine derivatives with meso -contiguous quaternary carbon centers were obtained with good to excellent enantioselectivities and diastereoselectivities from N a -unprotected or protected tryptamines. A formal asymmetric synthesis of hodgkinsine B was also executed to showcase its synthetic potential.