西索笼/铜（II）催化的高非对映选择性和对映选择性双环 N,O-缩醛的合成。
Cy-SaBOX/Copper(II)-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Bicyclic N,O Acetals.
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
出版信息
Angew Chem Int Ed Engl. 2016 Aug 1;55(32):9220-3. doi: 10.1002/anie.201603911. Epub 2016 Jun 28.
Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O-acetals is described. Cu(II) /SaBOX could catalyze the reaction of β,γ-unsaturated α-ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99 % yields; up to >95:5 d.r.; and 95-99 % ee). This reaction can be well performed on gram scale, even with only 1 mol % catalyst loading. The single-crystal structures of the copper complexes lead to a good understanding of the stereo-synergistic effects of the sidearm.
描述了一种用于构建双环 N,O-缩醛有用且重要骨架的简便、有效的方法。Cu(II)/SaBOX 可以有效地催化β,γ-不饱和α-酮酯与环烯胺的反应，从而以优异的收率和立体选择性（21 个实例；高达 99%的产率；高达>95:5 d.r.；95-99%ee）得到所需产物。该反应可以很好地在克级规模下进行，甚至只需 1 mol%的催化剂用量。铜配合物的单晶结构有助于很好地理解支链的立体协同效应。
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