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Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides
Author(s) -
Clavier Hervé,
Lepronier Aymeric,
BengobesseMintsa Nathalie,
Gatineau David,
Pellissier Hélène,
Giordano Laurent,
Tenaglia Alphonse,
Buono Gérard
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200903
Subject(s) - palladium , cycloaddition , norbornene , catalysis , chemistry , bicyclic molecule , phosphine , phosphine oxide , enantioselective synthesis , oxide , combinatorial chemistry , transformation (genetics) , organic chemistry , medicinal chemistry , polymer , monomer , biochemistry , gene
An efficient palladium‐catalyzed [2+1] cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalladacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of aminomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept‐2‐enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion.