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Chemo‐ and Diastereoselective Construction of Indenopyrazolines via a Cascade aza‐Michael/Aldol Annulation of Huisgen Zwitterions with 2‐Arylideneindane‐1,3‐diones
Author(s) -
Li Yuming,
Zhang Haikun,
Wei Rong,
Miao Zhiwei
Publication year - 2017
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.201701013
Subject(s) - annulation , stereocenter , chemistry , aldol reaction , michael reaction , cascade , cascade reaction , organocatalysis , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , chromatography
Abstract A cascade aza‐Michael/Aldol annulation of 2‐arylideneindane‐1,3‐diones with in situ generated Huisgen zwitterions has been developed. This reaction afforded the desired products in moderate to good yields (up to 87%) with excellent chemo‐ and diastereoselectivity (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important indenopyrazoline derivatives containing two contiguous chiral centers including a quaternary stereogenic center.