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Assembly of Enantioenriched cis ‐3a,8a‐Hexahydropyrrolo[2,3‐ b ]indole Scaffolds by Silver(I)‐Catalyzed Asymmetric Domino Reaction of Isocyanoacetates in the Presence of Cinchona ‐Derived Chiral Phosphorus Ligands
Author(s) -
Cheng Hengguang,
Zhang Runmei,
Yang Shiwei,
Wang Min,
Zeng Xiaofei,
Xie Lingjie,
Xie Chunsong,
Wu Jing,
Zhong Guofu
Publication year - 2016
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.201500538
Subject(s) - chemistry , domino , indole test , catalysis , cinchona alkaloids , combinatorial chemistry , cascade reaction , enantioselective synthesis , reaction conditions , cinchona , organic chemistry , stereochemistry
Abstract By using Cinchona ‐derived chiral phosphines as catalytic ligands, enantioenriched cis ‐3a,8a‐hexahydropyrrolo[2,3‐ b ]indoles ( ent ‐HPIs), which are core scaffolds in a large array of biologically active natural products, can be convergently assembled under mild conditions through the silver(I)‐catalyzed asymmetric domino reaction of readily available isocyanoacetates and 2‐(2‐aminophenyl)acrylates. Various functionalities can be tolerated in the reaction, affording enantioenriched HPIs in high overall yields and good enantioselectivities (up to 92% ee s).