Platinum(II) Catalysts for Highly Enantioselective 1,6-Enyne Cycloisomerizations. Synthetic, Structural, and Catalytic Studies

A new family of cyclometalated (N-heterocyclic carbene)-PtII complexes bearing monodentate phosphines as ancillary ligands has been designed for use as precatalysts in 1,6-enyne cycloisomerization reactions. Highly enantioselective skeletal rearrangements of allylpropargyl-tosylamide derivatives hav...

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Bibliographic Details
Published in:Organic letters 2009-05, Vol.11 (10), p.2137-2139
Main Authors: Brissy, Delphine, Skander, Myriem, Jullien, Hélène, Retailleau, Pascal, Marinetti, Angela
Format: Article
Language:English
Subjects:
Alkynes
Alkynes - chemistry
Catalysis
Cellular Biology
Cyclization
Heterocyclic Compounds, 1-Ring
Heterocyclic Compounds, 1-Ring - chemical synthesis
Heterocyclic Compounds, 1-Ring - chemistry
Life Sciences
Organometallic Compounds
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Platinum
Platinum - chemistry
Stereoisomerism
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Summary:A new family of cyclometalated (N-heterocyclic carbene)-PtII complexes bearing monodentate phosphines as ancillary ligands has been designed for use as precatalysts in 1,6-enyne cycloisomerization reactions. Highly enantioselective skeletal rearrangements of allylpropargyl-tosylamide derivatives have been developed by using (S)-Ph-Binepine as the chiral auxiliary. Enantiomeric excesses up to 97% have been obtained.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900724z