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Synthesis of Azaheterocyclic Vinylphosphonates by Ring‐Closing Metathesis
Author(s) -
Garzon Cécile,
Attolini Mireille,
Maffei Michel
Publication year - 2013
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.201300375
Subject(s) - ring closing metathesis , chemistry , ruthenium , metathesis , mitsunobu reaction , ring (chemistry) , salt metathesis reaction , combinatorial chemistry , catalysis , organic chemistry , stereochemistry , polymerization , polymer
The title compounds were synthesized by ruthenium‐catalyzed ring‐closing metathesis of N ‐tosyl‐ N ‐(ω‐alkenyl)aminomethylvinyl phosphonates, which were obtained from N ‐(ω‐alkenyl)‐ N ‐tosylamides. These compounds, in turn, were prepared from unsaturated alcohols through the Mitsunobu reaction. This methodology gives access to five‐ and six‐membered ring compounds. Additionally, chiral phosphonates can be obtained easily.