Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons.
[reaction: see text]. A novel and versatile strategy for the synthesis of highly functionalized substituted 3-sulfolenes based on [CpRu(CH3CN)3]PF6-catalyzed hydrative cyclization has been developed. A marked ketone directing effect in ruthenium-catalyzed cyclization was observed for the first time. This provides complementary chemoselectivity for the synthesis of 3-sulfolenes and other cyclic enones. The utility of this method has been demonstrated by SO2 extrusion of 3-sulfolenes to afford 1,3-dienes and the subsequent inter- and intramolecular Diels-Alder reaction.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Huang
Xiaojun
X
D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D007659:Ketones; D009942:Organometallic Compounds; D013450:Sulfones; D012428:Ruthenium