Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
Org Lett. 2017 Jul 7;19(13):3490-3493. doi: 10.1021/acs.orglett.7b01471. Epub 2017 Jun 28.
We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.
我们报告了通过亚胺和环氧化物的反极性偶联直接制备含有多达三个连续手性中心的 1,3-氨基醇。从亚胺生成的亲核 2-氮烯丙基阴离子，立体选择性地加成到环氧化物上，水解产物亚胺后得到 1,3-氨基醇。这些转化提供了氨基醇，其对两个反应伙伴的位点选择性均大于 98%，产率高达 98%以上，dr 值大于 20:1。
