Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 7, Issue 10, Pages 2446-2449Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201200481
Keywords
1; 2-addition; 3-substituted-3-hydroxy-2-oxindole; boron; isatin; ruthenium
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [B01]
- Grants-in-Aid for Scientific Research [22550092] Funding Source: KAKEN
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A chiral O-linked C2-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2-oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh3)3]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90?% ee. It was found that the reaction with N-protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the nitrogen atom were different depending on the substituents on the aromatic ring. The use of a N-benzyl group resulted in excellent enantioselectivities in many substrates compared with other groups.
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