通过环氧化和开环反应合成具有三个相邻手性中心的几乎对映体纯的氨基二醇。
Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening.
作者信息
Luo Lan, Yamamoto Hisashi
机构信息
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
出版信息
Org Biomol Chem. 2015 Nov 14;13(42):10466-70. doi: 10.1039/c5ob01808k. Epub 2015 Oct 6.
Abstract
A virtually complete enantioselective synthesis of 3-amino-1,2-diols with three consecutive stereocenters was accomplished by a sequential cascade of two kinetic resolutions, which features a Sharpless or Hafnium-catalyzed asymmetric epoxidation and a subsequent W-catalyzed aminolysis. Enantiopure products with up to >99.9% ee and >99.9 : 0.1 dr were obtained and could serve as potential building blocks for pharmaceutical or biological significant molecules.
摘要
通过两个动力学拆分的连续串联反应，实现了具有三个连续立体中心的3-氨基-1,2-二醇的几乎完全对映选择性合成，该反应以Sharpless或铪催化的不对称环氧化以及随后的钨催化氨解为特征。获得了对映体纯的产物，其对映体过量（ee）高达>99.9%，非对映体比例（dr）>99.9:0.1，可作为具有药物或生物学意义的重要分子的潜在构建单元。
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