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Improved resolution methods for (R,R)- and (S,S)-cyclohexane-1,2-diamine and (R)- and (S)-BINOL
Tetrahedron: Asymmetry Pub Date : 19 September 2003 , DOI: 10.1016/s0957-4166(03)00586-x
Hans-Jörg Schanz , Michael A Linseis , Declan G Gilheany

Starting from inexpensive l-(+)-tartaric acid, it was possible to resolve and obtain pure both enantiomers of trans-cyclohexane-1,2-diamine 1 and thence both enantiomers of BINOL 2, two of the most powerful, chiral inducing backbones in asymmetric catalysis. The modified method is very economic, not only due to an almost doubling of the overall yields of enantiomerically pure compounds (86% 1, 83% 2) but also due to the easy recovery of resolving agent 1 [66% (R,R)-1, 79% (S,S)-1] in the BINOL resolution. An improvement in the yield of the preparation of racemic BINOL is also recorded.

中文翻译:

RR)-和(SS)-环己烷-1,2-二胺以及(R)-和(S)-BINOL的改进拆分方法

从廉价的L-(+)-酒石酸开始,有可能解析并获得纯的反式-环己烷-1,2-二胺1的两种对映体,以及BINOL 2的两种对映体,这是两种功能最强的手性诱导骨架。在不对称催化中。修饰的方法是非常经济的,这不仅是由于几乎加倍映体纯化合物(86%的总产率的1,83%2),而且还由于拆分剂的易回收1 [66%([R - [R )- 1,79%(小号小号) - 1在BINOL分辨率中。还记录了外消旋BINOL的制备产率的提高。
更新日期:2017-01-31
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