从炔基环氧乙烷便捷获取官能化乙烯基环戊烯醇。
Convenient access to functionalized vinylcyclopentenols from alkynyloxiranes.
作者信息
Wang Letian, Maddess Matthew L, Lautens Mark
机构信息
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
出版信息
J Org Chem. 2007 Mar 2;72(5):1822-5. doi: 10.1021/jo062107w. Epub 2007 Feb 7.
Beta,gamma-alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF3.OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.
通过用催化量的三氟甲磺酸钪（Sc(OTf)₃）或三氟化硼乙醚（BF₃·OEt₂）处理炔基环氧乙烷原位生成的β,γ-炔基醛，能被多种烯丙基亲核试剂有效捕获，以良好的产率和选择性得到高炔丙基高烯丙醇。这类产物用作通过烯炔复分解反应合成官能化乙烯基环戊烯醇的底物。
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