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( E )‐Dimethyl 2‐Oxopent‐3‐enylphosphonate: An Excellent Substrate for Cross‐Metathesis – Easy Access to Functionalized Heterocycles
Author(s) -
Cochet Thomas,
Roche Didier,
Bellosta Véronique,
Cossy Janine
Publication year - 2012
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.201101398
Subject(s) - chemistry , metathesis , tandem , salt metathesis reaction , microwave irradiation , ring closing metathesis , catalysis , combinatorial chemistry , side chain , substrate (aquarium) , surface modification , organic chemistry , polymerization , materials science , oceanography , composite material , geology , polymer
Simple and efficient access to tetrahydrofurans, tetrahydropyrans, and pyrrolidines through a tandem cross‐metathesis/1,4‐addition process from ( E )‐dimethyl 2‐oxopent‐3‐enylphosphonate and N ‐protected ω‐unsaturated amines or alcohols under microwave irradiation is described. As the Grubbs–Hoveyda catalyst is highly chemoselective, a diversity of functionalized heterocycles were synthesized. Furthermore, an additional functionalization can be performed due to the presence of a side chain that possesses a ketophosphonate at the C2 position of the heterocycle.