Premium
Olefin‐Metathesis‐Based Synthesis of Furans by an RCM/Deprotonation/Phosphorylation Sequence and Their Diels–Alder Reactions
Author(s) -
Schmidt Bernd,
Geißler Diana
Publication year - 2011
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.201101078
Subject(s) - chemistry , deprotonation , electrophile , diels–alder reaction , metathesis , ring closing metathesis , olefin metathesis , amide , organic chemistry , salt metathesis reaction , stereochemistry , medicinal chemistry , catalysis , polymer , polymerization , ion
Butenolides, obtained by ring‐closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent Diels–Alder reaction and acid‐catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes.