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Rhodium(II)‐Catalyzed Reaction of 1‐Tosyl‐1,2,3‐triazoles with Morita–Baylis–Hillman Adducts: Synthesis of 3,4‐Fused Pyrroles
Author(s) -
Jia Renmeng,
Meng Jiang,
Leng Jiaying,
Yu Xingxin,
Deng WeiPing
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800057
Subject(s) - rhodium , chemistry , adduct , intramolecular force , aromatization , methyl vinyl ketone , tosyl , catalysis , sigmatropic reaction , ketone , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
A cascade reaction of rhodium azavinylcarbenes with Morita–Baylis–Hillman (MBH) adducts enables a novel synthetic approach to 3,4‐fused pyrroles. The cascade reaction begins with the insertion of O−H bond into rhodium azavinylcarbenes, subsquent sigmatropic rearrangement provides substituted α,β‐unsaturated cyclic ketone intermediates. Then the intramolecular aza Michael addition/oxidative aromatization sequence give rise to a wide range of 3,4‐fused pyrroles in good yields, and with excellent functional group compatibility.