Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 3, Pages 1594-1602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12493
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Funding
- JSPS KAKENHI [15H05803, 18K14219, 17H05371, 19H04580, 17H03057, 18H02459]
- Grants-in-Aid for Scientific Research [17H03057, 17H05371, 15H05803, 19H04580, 18K14219, 18H02459] Funding Source: KAKEN
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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).
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