S. Chou, Chin-Lu Tseng, Shyh-Fong Chen
May 21, 2000
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0
Influential Citations
4
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4-yn-3-ol ( 1 ) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation ( E : Z =9:1 max ). The resulting ( E )-1-halo-6,6-dimethyl-2-hepten-4-yne ( 2 ), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally related enyne alcohols have been studied likewise and shown similar versatility.