手性环氧化物通过螺环硼酸酯酯催化的 2-卤代酮的硼烷还原：在光学纯 1,2-羟基醚和 1,2-叠氮醇合成中的应用。
Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.
机构信息
Department of Chemistry, University of Puerto Rico-H-umacao, CUH Station, Humacao, Puerto Rico 00791.
出版信息
J Org Chem. 2011 Mar 18;76(6):1883-6. doi: 10.1021/jo102294j. Epub 2011 Feb 4.
Abstract
An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield.
摘要
本文描述了一种对映选择性硼烷介导的多种 2-卤代酮还原反应，使用 10%的螺环氨基硼酸酯 1 作为催化剂。通过简单的碱性后处理，得到了光学活性的环氧化合物，产率高，对映选择性极好（高达 99%ee）。在不同的反应条件下，研究了环氧化合物与苯氧基或叠氮化钠的开环反应，得到了非外消旋的 1,2-羟基醚和 1,2-叠氮醇，具有极好的对映选择性（99%ee）和良好到高的化学产率。
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