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Pd(0)‐Catalyzed Bismetallative Cyclization of Enynes in the Presence of Bu 3 SnSiMe 3 Using N ‐Heterocyclic Carbene as a Ligand
Author(s) -
Sato Yoshihiro,
Imakuni Noriko,
Mori Miwako
Publication year - 2003
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.200390055
Subject(s) - chemistry , carbene , moiety , ligand (biochemistry) , nucleophile , salt (chemistry) , vinylsilane , catalysis , medicinal chemistry , alkyl , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry
It was found that a nucleophilic N ‐heterocyclic carbene could be utilized as a ligand for Pd(0)‐catalyzed bismetallative cyclization of enynes in the presence of Bu 3 SnSiMe 3 . An imidazolium salt having a bulky alkyl group attached to both nitrogen atoms of its imidazol‐2‐ylidene skeleton or an imidazolinium salt is suitable as a ligand precursor. The cyclized products obtained from this cyclization have both a vinylsilane moiety and a homoallylstannane moiety, whose utility in synthetic organic chemistry has been proven by transformation into cyclopropanol derivatives.