期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 3, 页码 1594-1602出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12493
关键词
-
资金
- JSPS KAKENHI [15H05803, 18K14219, 17H05371, 19H04580, 17H03057, 18H02459]
- Grants-in-Aid for Scientific Research [17H03057, 17H05371, 15H05803, 19H04580, 18K14219, 18H02459] Funding Source: KAKEN
gamma-Lactam derivatives with multiple contiguous stereogenic carbon centers are ubiquitous in physiologically active compounds. The development of straightforward and reliable synthetic routes to such chiral structural motifs in a stereocontrolled manner should thus be of importance. Herein, we report a strategy to construct polycyclic gamma-lactam derivatives that contain more than two contiguous stereogenic centers in an enantioselective as well as atom-economic manner. Moreover, we have achieved the first enantioselective synthesis of strigolactam derivative GR-24, a racemic variant of which is a potential seed germination stimulator and plantgrowth regulator. A key of the procedure presented here is a nickel(0)/chiral phosphoramidite-catalyzed asymmetric [2+2+1] carbonylative cycloaddition between readily accessible ene-imines and carbon monoxide, which proceeded enantioselectively to furnish up to 90% ee (>99% ee after recrystallization). The results of mechanistic studies, including the isolation of a chiral heteronickelacycle, support that the enantioselectivity on the two contiguous carbon atoms of the gamma-lactams is determined during the oxidative cyclization on nickel(0).
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据