Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols.
Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols.
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DOI：
10.1021/acs.orglett.7b01049
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发表时间：
2017-05
期刊：
影响因子：
5.2
通讯作者：
Rachael Pittaway;J. Fuentes;M. Clarke
中科院分区：
文献类型：
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作者：
Rachael Pittaway;J. Fuentes;M. Clarke
以易得的烯丙基甘氨酸为原料，采用Rh/（S，S，S）-BOBPHOS催化剂，通过串联的氢甲酰化-半缩醛胺反应合成了手性功能化哌啶，具有很好的非对映选择性和支化区域选择性。串联氢甲酰化-半缩醛形成也以良好的非对映选择性（88：12）进行，半缩醛产物被氢化并保留立体化学，得到用于合成新型抗生素奈莫沙星的手性中间体。
Starting from readily available allylglycine, a tandem hydroformylation-hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation-hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin.