对映选择性有机催化 α-当归内酯与 β-卤代-α-酮酯的加成反应。
Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.
机构信息
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
出版信息
J Org Chem. 2017 Feb 17;82(4):2276-2280. doi: 10.1021/acs.joc.6b03059. Epub 2017 Feb 6.
Abstract
A quinidine-catalyzed diastereoselective addition of α-angelica lactone to β-halo-α-ketoesters is reported. The α-angelica lactone displays unusual regioselectivity in this reaction, acting as a nucleophile at the α-position to provide fully substituted glycolic esters with three contiguous stereocenters. Subsequent diastereoselective hydrogenation provides an additional stereocenter within the lactone.
摘要
报道了一种奎尼丁催化的α-当归内酯与β-卤代-α-酮酯的非对映选择性加成反应。在该反应中，α-当归内酯表现出异常的区域选择性，作为亲核试剂进攻α-位，提供具有三个连续立体中心的全取代甘醇酸酯。随后的非对映选择性氢化在内酯中引入了另一个立体中心。
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Chem Sci. 2015 Nov 1;6(11):6086-6090. doi: 10.1039/C5SC02170G. Epub 2015 Jul 30.
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