期刊
ORGANIC LETTERS
卷 20, 期 20, 页码 6564-6568出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02902
关键词
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资金
- NSFC [21472123, 21620102003, 21572129, 21831005]
- STCSM [18ZR1431700]
- SHMEC [201701070002E00030]
The asymmetric allylation of 1-pyrroline-5-carboxylic esters has been accomplished through a synergistic Pd/Cu catalyst system under mild reaction conditions. The mechanistic studies suggested that (1) nucleophilic attack is the enantiodiscriminating step; (2) the cooperative action of two chiral reactive species, N-metalated azomethine ylides and pi-allylpalladium, is most likely responsible for its high reactivity and excellent enantioselectivity (up to >99% ee); and (3) the steric hindrance and electronic factors of the allylic electrophiles and imino ester substrates are crucial for the formation of the linear products. A series of 3,4-2H-pyrrole derivatives bearing a quaternary stereogenic center were easily synthesized in high yields and with high to excellent regioselectivity and enantioselectivity.
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