Gold- vs. Platinum-Catalyzed Polycyclizations by O-Acyl Migration. Solvent-Free Reactions

Polycyclic derivatives incorporating a cyclopropyl group have been efficiently synthesized from propargyl acetates using platinum(II), gold(I) and gold(III) catalysis. These reactions which are also viable for the preparation of medium‐sized rings, proceed with a complete diastereocontrol and can al...

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Published inAdvanced synthesis & catalysis Vol. 350; no. 1; pp. 43 - 48
Main Authors Moreau, Xavier, Goddard, Jean-Philippe, Bernard, Matthieu, Lemière, Gilles, López-Romero, Juan Manuel, Mainetti, Emily, Marion, Nicolas, Mouriès, Virginie, Thorimbert, Serge, Fensterbank, Louis, Malacria, Max
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 04.01.2008
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
cyclopropanes
enynes
gold
Physical Sciences
platinum
Science & Technology
solvent-free reactions
ELECTROPHILIC ACTIVATION
POLYFUNCTIONALIZED 1,6-ENYNES
CYCLOPROPANATION
cyclopropanes
MECHANISMS
HYDROAMINATION
enynes
PTCL2-MEDIATED CYCLOISOMERIZATION
solvent-free reactions
gold
ALKENES
platinum
INTERCEPTION
HYDROARYLATION
(-)-CUBEBOL
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Summary:Polycyclic derivatives incorporating a cyclopropyl group have been efficiently synthesized from propargyl acetates using platinum(II), gold(I) and gold(III) catalysis. These reactions which are also viable for the preparation of medium‐sized rings, proceed with a complete diastereocontrol and can also be run in neat conditions.
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200700356