期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 11, 页码 4418-4421出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900502d
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Grants-in-Aid for Scientific Research [20390002] Funding Source: KAKEN
Catalytic asymmetric synthesis of neolignan natural products (-)-epi-conocarpan and (+)-conocarpan has been achieved by exploiting an enantio- and diastereoselective intramolecular C-H insertion reaction to construct a cis-2-aryl-2,3-dihydrobenzofuran ring system as a key step. The C-H insertion reaction of 5-bromoaryldiazoacetate catalyzed by Rh-2(S-PTTEA)(4), a new dirhodium(II) carboxylate complex that incorporates N-phthaloyl-(S)-triethylalaninate as chiral bridging ligands, provided 2-aryl-5-bromo-3-methoxycarbonyl-2,3-dihydrobenzofuran with exceptionally high diastereoselectivity (cis/trans = 97:3) and high enantioselectivity for the cis isomer (84% ee).
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