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Asymmetric Direct Remote Michael Addition Reactions of Allyl Furfurals via Dearomative Trienamine and Tetraenamine Catalysis
Author(s) -
Xu ChangJiang,
Li HongWei,
He XiaoLong,
Du Wei,
Chen YingChun
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900197
Subject(s) - chemistry , regioselectivity , furfural , amine gas treating , michael reaction , isatin , bifunctional , catalysis , thiourea , organic chemistry , organocatalysis , combinatorial chemistry , enantioselective synthesis
Abstract 2‐Allyl‐3‐furfural could generate dearomative trienamine species in the presence of a chiral secondary amine, and underwent an asymmetric remote ϵ‐regioselective Michael addition reaction with isatin‐derived α,α‐dicyanoalkenes. Meanwhile, the more challenging dearomative tetraenamine intermediate from 5‐allyl‐2‐furfural could be similarly utilized in very remote η‐regioselective Michael additions. In general, good yields with moderate to high enantioselectivity were obtained by employing a concerted activation strategy of bifunctional secondary amine/thiourea catalysts.