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Cyclobutene Formation in PtCl 2 ‐Catalyzed Cycloisomerizations of Heteroatom‐Tethered 1,6‐Enynes
Author(s) -
Ni Zhenjie,
Giordano Laurent,
Tenaglia Alphonse
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403643
Subject(s) - cyclobutene , heteroatom , chemistry , catalysis , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry)
Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl 2 ‐catalyzed cycloisomerizations of heteroatom‐tethered 1,6‐enynes featuring a terminal alkyne and amide as the solvent. It is shown that the weak coordinating properties of the solvent and alkyl substituent(s) at the propargylic carbon atom favor the formation of cyclobutenes instead of other possible cycloisomerization products such as 1,3‐diene derivatives or cyclopropane‐fused heterocycles.