A biocatalytic/reductive etherification approach to substituted piperidinyl ethers
作者:Jeffrey T. Kuethe、Jacob M. Janey、Matthew Truppo、Juan Arredondo、Tao Li、Kelvin Yong、Shuwen He
DOI:10.1016/j.tet.2014.04.064
日期:2014.7
synthetically useful protocol has been developed for the preparation of highly functionalized piperidinyl ethers. Biocatalytic reduction of cyclhexanones 7, 10, and 14 allows for the preparation of both cis- and trans diastereomers with an extremely high degree of stereochemical control. Reductive etherification of the corresponding trimethylsilylethers with 1-(benzyloxycarbonyl)-4-piperidinone 17 in the presence
已经开发出用于制备高度官能化的哌啶基醚的合成上有用的方案。生物催化还原cyclhexanones的7,10,和14允许用于制备两者的顺式-和反式非对映体具有极高程度的立体化学控制的。相应的三甲基甲硅烷基醚与1-(苄氧羰基)-4-哌啶酮17的还原醚化在三乙基硅烷和催化TMSO-Tf的存在下,以良好或优异的收率提供了所需的哌啶基醚。最终,氮保护基的湿解产生了接近定量产率的哌啶基醚。还介绍了该方法在一系列哌啶醚中的应用,包括二苯基吡咯啉和依巴斯汀的核心骨架。