一种制备对映体纯脱氧丙酸酯亚基的迭代催化路线：格氏试剂对α,β-不饱和硫酯的不对称共轭加成。
An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated thioesters.
作者信息
Des Mazery Renaud, Pullez Maddalena, López Fernando, Harutyunyan Syuzanna R, Minnaard Adriaan J, Feringa Ben L
机构信息
Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
出版信息
J Am Chem Soc. 2005 Jul 20;127(28):9966-7. doi: 10.1021/ja053020f.
A highly enantioselective (up to 96% ee) conjugate addition of Grignard reagents, in particular, MeMgBr, to alpha,beta-unsaturated thioesters is provided as well as its application to a diastereo- and enantioselective iterative route to syn- and anti-1,3-dimethyl arrays and deoxypropionate subunits. The versatility of the method is illustrated in the synthesis of (-)-lardolure, a multimethyl-branched insect natural pheromone.
提供了格氏试剂，特别是甲基溴化镁，对α,β-不饱和硫酯的高度对映选择性（高达96% ee）共轭加成反应，以及该反应在合成顺式和反式-1,3-二甲基阵列和脱氧丙酸酯亚基的非对映和对映选择性迭代路线中的应用。该方法的通用性在多甲基支链昆虫天然信息素（-）-诱虫烯的合成中得到了体现。
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