期刊
SCIENCE CHINA-CHEMISTRY
卷 64, 期 11, 页码 1985-1989出版社
SCIENCE PRESS
DOI: 10.1007/s11426-021-1069-7
关键词
ynamides; cyclization; lactams; diastereoselectivity; N-heterocycles
资金
- National Natural Science Foundation of China [92056104, 21772161]
- Natural Science Foundation of Fujian Province of China [2019J02001]
- Xiamen University [20720210002]
- National Fund for Fostering Talents of Basic Science (NFFTBS) [J1310024]
- Opening Project of PCOSS, Xiamen University [201909]
- Bioinformatics Center of Nanjing Agricultural University
- Start-up Research Fund of Nanjing Agricultural University [050-804099]
A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides has been developed for the efficient and practical synthesis of medium-sized lactams (7- to 9-membered rings), showing a totally inverse diastereoselectivity compared to traditional methods. The protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities. Additionally, a rational mechanism based on theoretical calculations has been proposed to explain the inversion of diastereoselectivity.
A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides for efficient and practical synthesis of medium-sized lactams (7- to 9-membered rings) is disclosed. Compared with previous hydrative cyclization for the formation of six-membered lactams (cis-form), a totally inverse diastereoselectivity (trans-form) of medium-sized lactams is observed. In addition, this protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities. Moreover, a rational mechanism to understand this inversion of diastereoselectivity is proposed based on theoretical calculations.
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