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Organocatalyzed Asymmetric Dearomative [3+2] Annulation of Electron‐Deficient 2‐Nitrobenzo Heteroarenes with 3‐Isothiocyanato Oxindoles
Author(s) -
Dou PeiHao,
Chen Yan,
You Yong,
Wang ZhenHua,
Zhao JianQiang,
Zhou MingQiang,
Yuan WeiCheng
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100516
Subject(s) - chemistry , bifunctional , annulation , stereocenter , thiourea , catalysis , organocatalysis , substrate (aquarium) , yield (engineering) , enantioselective synthesis , medicinal chemistry , hydrogen bond , combinatorial chemistry , organic chemistry , molecule , oceanography , materials science , geology , metallurgy
An organocatalyzed asymmetric dearomative [3+2] annulation reaction of electron‐deficient 2‐nitrobenzo heteroarenes including 2‐nitrobenzofurans, 2‐nitrobenzothiophenes and 2‐nitroindoles with 3‐isothiocyanato oxindoles was developed. With a multiple hydrogen‐bonding bifunctional thiourea as the catalyst, the reaction displays broad substrate scope and provides an access to structurally diverse polycyclic spirooxindoles containing three contiguous stereogenic centers in high yields with good diastereo‐ and enantioselectivities (up to 99% yield, 94:6 dr, and 97% ee). This organocatalysis protocol is able to afford the products with complementarily diastereoselectivity versus the previous work with transition metal catalysis.