期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 13, 页码 6687-6696出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00835
关键词
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资金
- Ministry of Education, Science and Culture, Japan [20200052, 24550116]
- Grants-in-Aid for Scientific Research [24550116, 20200052, 15K05497] Funding Source: KAKEN
Asymmetric 1,3-dipolar cycloaddition reactions between N-methylindoles and several cyclic carbonyl ylides that were derived from diazodiketone or diazoketoester precursors in the presence of both achiral Rh and chiral lanthanoid metal catalysts are described. For the six-membered cyclic carbonyl ylides derived from 1-diazo-5-aryl-2,5-pentanedione precursors, the cycloaddition reactions were carried out using Rh-2(OAc)(4) (2 mol %) and the chiral Pybox-Ph-2 -Lu(OTf)(3) complex (10 mol %) as catalysts, resulting in high enantioselectivities (83% to >98% ee (exo)) along with relatively good exo-selectivities (exo:endo = 65:35 to 94:6) and yields (63-85%). For the five-membered cyclic carbonyl ylide derived from bromo-1-methylindole was carried out in the presence of Rh-2(OAc)(4) (2 mol%) and chiral Pybox-Ph-2-Er(OTf)(3) complex (30 mol %) as catalysts, resulting in relatively good enantioselectivity (78% ee) and endo-selectivity (endo:exo = 81:19).
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