title: Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: [4 + 2] annulation and enyne cross metathesis.
abstract: A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to α,β-unsaturated δ-lactones, for which preliminary asymmetric reactions were also demonstrated. For 1,2-disubstituted alkenes, unprecedented enyne cross metathesis occurred to give 1,3-dienes in a completely stereospecific fashion. DFT calculations and experiments indicated that the cyclobutene derivatives are not viable intermediates and that the steric interactions during concerted σ-bond rearrangements are responsible for the observed unique stereospecificity.
authors: Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea.
authors: Hyun-Suk
authors: HS
authors: Yeom
authors: Jaeyoung
authors: J
authors: Koo
authors: Hyun-Sub
authors: HS
authors: Park
authors: Yi
authors: Y
authors: Wang
authors: Yong
authors: Y
authors: Liang
authors: Zhi-Xiang
authors: ZX
authors: Yu
authors: Seunghoon
authors: S
authors: Shin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000480:Alkynes; D011422:Propionates; D006046:Gold; C011537:propiolic acid