Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically pure (-)-α-Thujone

Article Article scientifique Article Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically pure (-)-α-Thujone eng 1997 author Von Oppolzer Wolfgang 25270 author Pimm Austen David 29325 author Stammen Blanda Luzia Christa 29417 author Hume Ewan 98510 623-639 10.1002/hlca.19970800302 0018-019X http://doi.wiley.com/10.1002/hlca.19970800302 Intramolecular [Pd2(dba)3]/tri(2‐furyl)phosphine‐catalysed (dba = dibenzylideneacetone, PhCH=CHCOCH=CHPh) cyclisations of olefinic propargylic carbonates I provided alk‐1‐enyl‐(3‐aza)bicyclo[3.1.0]‐hexanes VIII in good yields. A palladium cascade sequence I → II → III → IV → VII → VIII is proposed. Furthermore, chiral propargylic carbonates such as 23, 24 and 25 allowed diastereoselective formation of bicyclo[3.1.0]hexanes 29, 30 and 31, respectively. The first diastereoselective synthesis of the monoterpene, (−)‐α‐thujone 40 illustrates the potential of the method. Dewey 540 36 Département de chimie organique 141 false Helvetica Chimica Acta 80 3 ae51279a-3859-4b31-9f40-a9b7c9f28169 Article (Published version) Restricted Oppolzer_et_al-1997-Helvetica_Chimica_Acta.pdf 1127979 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically pure (-)-α-Thujone	Helvetica Chimica Acta			1997	325	0

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Pimm, Austen David