期刊
CHEMISTRYSELECT
卷 3, 期 18, 页码 5216-5219出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201801233
关键词
Alkaloids; Allylic substitution; Asymmetric catalysis; Heterocycles; Stereoselectivity
资金
- Deutsche Forschungsgemeinschaft [Br 604/16-1/16-2/16-3]
N-Deprotonated five-, six-, seven, and nine-membered lactams undergo smooth palladium-catalyzed N-allylation with methyl-(pent-3-en-2-yl)-carbonate or 2-chloro-3-pentene. With axially chiral bisphosphane ligands, enantioselectivities ranging from 83 to 97% ee are reached. The configuration of one of the allylation products is assigned unambiguously by the preparation of a relay compound and by analogy to the others. Using the enantioselective allylation protocol as a key step, delta-valerolactam is converted into (4S,9aR)-4-methylquinolizidine.
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