Department of Respiratory and Critical Care Medicine, Institute of Respiratory Health, State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, No. 17 Renmin Nan Road, Chengdu 610041, China.
Org Lett. 2022 Oct 28;24(42):7763-7768. doi: 10.1021/acs.orglett.2c03090. Epub 2022 Oct 18.
The first Ni-catalyzed asymmetric reductive coupling of 2-aza-butadiene with aldehydes was achieved to synthesize chiral γ-secondary amino alcohols. This transformation features good enantioselectivity and tolerance to various functional groups, which may serve as a complementary method to previously reported noble-metal-catalyzed protocols. Through competition reaction, 2-aza-butadiene was proved to be a more reactive coupling component than its full-carbon analogue, 1,3-butadiene. Notably, this reaction delivers β-siloxyl imine, an aza-aldol-type product which is difficult to access by conventional methods.
首例镍催化的 2-氮杂丁二烯与醛的不对称还原偶联反应被实现，从而合成了手性γ-仲氨基醇。该转化具有良好的对映选择性和对各种官能团的耐受性，可作为对先前报道的贵金属催化方案的补充方法。通过竞争反应，证明 2-氮杂丁二烯比其全碳类似物 1,3-丁二烯具有更高的反应性。值得注意的是，该反应得到了β-硅氧基亚胺，这是一种通过传统方法难以获得的氮杂-羟醛型产物。
