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Tuning the Chemoselectivity of the Metathesis Reactions of N ‐Substituted 2‐Azabicyclo[2.2.1]hept‐5‐en‐3‐one
Author(s) -
Aljarilla Ana,
Plumet Joaquín
Publication year - 2008
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.200800450
Subject(s) - metathesis , chemistry , alkene , chemoselectivity , salt metathesis reaction , ring closing metathesis , acyclic diene metathesis , ring opening metathesis polymerisation , ring (chemistry) , ethylene , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , polymerization , polymer
By using the second‐generation Hoveyda–Grubbs precatalyst, the metathesis transformations of N ‐substituted 2‐azabicyclo[2.2.1]hept‐5‐en‐3‐one derivatives have been explored. In the absence of any external alkene (cross‐metathesis partner), substituted pyrrolizidin‐3‐one derivatives were obtained by ring‐opening metathesis/ring‐closing metathesis tandem reactions. In the presence of an external alkene, N ‐substituted 2‐pyrrolidinones were isolated by ring‐opening metathesis/cross metathesis tandem reactions. In this case, and by using an alkene other than ethylene (allyltrimethylsilane), the reaction was totally chemo‐ and diastereoselective. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)