Bis(mandelato)borate: an effective, inexpensive spiroborate anion for chiral resolution
作者:Lawrence W-Y. Wong、Jack W-H. Kan、Thanh-ha Nguyen、Herman H-Y. Sung、Dang Li、Alex S-F. Au-Yeung、Rajpal Sharma、Zhenyang Lin、Ian D. Williams
DOI:10.1039/c5cc04977f
日期:——
Cations of tetrahydropalmatine (THP), 1,2-diaminopropane (1,2-dap) and [Co(phen)3]3+ are all readily resolved by the red [BS(R-Man)2] anions with >90% ee in 1 easy step.
(1′S,5R,S)-(1′-phenyleth-1′-yl)-5-iodomethyl-imidazolines 4a,b have been synthesised and easily resolved by silica gel chromatography. The correlation between the configuration and the 1H NMR chemical shifts allows to assign the configuration at the C-5 of these intermediates. Each pure diastereomer has been converted to R(−)- and to S(+)-1,2-propyldiamine, respectively.
(1'S,5R,S)-(1'-苯基乙-1'-基)-5-碘甲基-咪唑啉4a,b已经合成,并且容易通过硅胶色谱法拆分。构型与1 H NMR化学位移之间的相关性允许在这些中间体的C-5处指定构型。每个纯的非对映异构体已分别转化为R(-)-和S(+)-1,2-丙基二胺。