Premium
Base‐Catalyzed Domino Michael–Alkylation–Rearrangement Reaction: A Synthetic Route to Functionalized 2,3‐Dihydrofurans
Author(s) -
Zhang RenZun,
Meng ChangYu,
Xie JianWu,
Xu MeiLan,
Zhu WeiDong
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402126
Subject(s) - chemistry , domino , cascade reaction , stereoselectivity , sulfonyl , catalysis , alkylation , substrate (aquarium) , combinatorial chemistry , base (topology) , rearrangement reaction , reaction conditions , medicinal chemistry , organic chemistry , mathematical analysis , alkyl , oceanography , mathematics , geology
An unexpected and efficient domino reaction of N ‐sulfonyl‐1‐aza‐1,3‐dienes with 2‐halo‐1,3‐dicarbonyl compounds to synthesize differently substituted 2,3‐dihydrofuran derivatives with excellent regio‐, chemo‐, and stereoselectivity in moderate to good yields was developed. In this transformation, broad substrate scope was demonstrated, and a plausible mechanism for this novel domino reaction was given.