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1,3‐dipolar addition of methyl α‐diazoacetoacetate to enamines: A new synthetic route to 5‐amino‐4,5‐dihydrofurans
Author(s) -
Huang Dan,
Yan Ming,
Zhao WeiJie,
Shen Qi
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040221206
Subject(s) - chemistry , intramolecular force , nucleophilic addition , nucleophile , medicinal chemistry , enamine , stereochemistry , catalysis , combinatorial chemistry , organic chemistry
The reaction of methyl a‐diazoacetoacetate with enamines catalyzed by dirhodium and copper complexes underwent formal 1,3‐dipolar addition to give 5‐amino‐4,5‐dihydrofurans in moderate yields. The reaction was suggested to proceed via a nucleophilic addition of enamines to metal‐carbenes and a subsequent intramolecular cyclization of the resulting zwitterionic intermediates.