Reiter Maud, Turner Hazel, Mills-Webb Rebecca, Gouverneur Véronique
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK.
J Org Chem. 2005 Oct 14;70(21):8478-85. doi: 10.1021/jo051274d.
A boron-mediated syn- and anti-stereoselective aldol reaction giving rise to various beta-hydroxyenones was coupled to a Pd((II))-mediated oxidative cyclization to give 2,3,6-trisubstituted syn- and anti-dihydropyranones in good yields. The Pd((II))-mediated oxidative cyclization was expanded to alpha-hydroxyenones leading to furan-3(2H)-one derivatives, which include natural product bullatenone and a known precursor of geiparvarin. The sole product of the oxidative cyclization of alpha,beta-dihydroxyenone was a five-membered furan-3(2H)-one derivative, suggesting that the ring closure of these diols is both chemo- and regioselective.
硼介导的合成各种β-羟基烯酮的顺式和反式立体选择性羟醛反应与钯（II）介导的氧化环化反应相偶联，以良好的产率得到2,3,6-三取代的顺式和反式二氢吡喃酮。钯（II）介导的氧化环化反应扩展到α-羟基烯酮，生成呋喃-3（2H）-酮衍生物，其中包括天然产物布拉特烯酮和已知的格帕瓦林前体。α,β-二羟基烯酮氧化环化的唯一产物是五元呋喃-3（2H）-酮衍生物，这表明这些二醇的闭环反应具有化学和区域选择性。
