Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof
Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof
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DOI：
10.1016/j.tet.2007.04.075
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发表时间：
2007-07-16
期刊：
影响因子：
2.1
通讯作者：
Lassaletta, Jose M.
中科院分区：
文献类型：
--
作者：
Fernandez, Rosario;Ros, Abel;Lassaletta, Jose M.
反式环烷基胺的非对映和对映选择性合成是通过三步反应完成的：(1)以HCO2H/Et3N为氢源，以TsDPEN为基的Ru(II)催化剂，通过动态动力学拆分双环和单环α-取代酮的不对称转移氢化反应；(2)在改进的Mitsunobu条件下，用二苯基磷叠氮将生成的顺环烷醇的亲核羟基还原为叠氮；(3)用PPh3/H2O的LiAlH4还原反式叠氮中间体。类似于2007爱思唯尔有限公司。保留所有权利。
The diastereo-and enantioselective syntheses of trans-cycloalkyl amines was accomplished through a three-step sequence consisting of: (1) asymmetric transfer hydrogenation through dynamic kinetic resolution of bicyclic and monocyclic alpha-substituted ketones using HCO2H/Et3N as the hydrogen source and TsDPEN-based Ru(II) catalysts, (2) nucleophilic hydroxyl to azide substitution of the resulting ciscycloalkanols using diphenyl phosphoryl azide under modified Mitsunobu conditions, and (3) reduction of the trans-azide intermediates with LiAlH4 of PPh3/H2O to the desired targets. similar to 2007 Elsevier Ltd. All rights reserved.