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Enantioselective Cycloisomerization of 1,5‐Enynes Promoted by Cyclometalated NHC–Pt II –Monophos Catalysts
Author(s) -
Jullien Hélène,
Brissy Delphine,
Retailleau Pascal,
Marinetti Angela
Publication year - 2011
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201100818
Subject(s) - stereocenter , cycloisomerization , chemistry , enantioselective synthesis , catalysis , enantiomer , carbon atom , stereochemistry , enantiomeric excess , carbon fibers , medicinal chemistry , organic chemistry , ring (chemistry) , materials science , composite number , composite material
The enantioselective cycloisomerizations of 1,5‐enynes bearing non‐migrating oxygen functions at the propargylic carbon atom have been carried out by using Monophos–Pt II and Binepine–Pt II complexes as chiral precatalysts. They afforded the corresponding bicyclo[3.1.0]hexan‐3‐one in up to 63 % enantiomeric excess. The stereochemical outcome of these reactions has been investigated in order to highlight possible matching–mismatching effects between the chiral catalyst and chiral substrates with opposite configurations at the stereogenic carbon. A substantial effect of the stereogenic carbon has been evidenced.