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Volumn 8, Issue 13, 2006, Pages 2715-2718

Rhodium-catalyzed addition of arylboronic acids to isatins: An entry to diversity in 3-aryl-3-hydroxyoxindoles

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; DRUG DERIVATIVE; INDOLE DERIVATIVE; ISATIN; RHODIUM;

EID: 33746147475     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0608101     Document Type: Article
Times cited : (183)

References (59)
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    • The synthesis of enantiomerically enriched 3-aryl-3-hydroxyoxindoles has been accomplished via the highly diastereoselective arylation of mandelic acid: (a) Barroso, S.; Blay, G.; Cardona, L.; Ferná, I.; García, B.; Pedro, J. R. J. Org. Chem. 2004, 69, 6821. For the synthesis of enantiomerically enriched 3-aryl-3-hydroxyoxindoles by asymmetric hydroxylation using chiral oxaziridines, see ref 2b.
    • (2004) J. Org. Chem. , vol.69 , pp. 6821
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  • 17
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    • Lee, S.1    Hartwig, J.F.2
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    • After submission of this manuscript, the group of Hayashi reported the rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins: Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353.
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3353
    • Shintani, R.1    Inoue, M.2    Hayashi, T.3
  • 31
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    • For a recent review on enantioselective addition to ketones using zinc reagents, see: (a) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284.
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    • For leading references in the field of catalytic enantioselective additions of organometallic aryl and alkenyl reagents to carbonyl compounds, see: (b) García, C.; Walsh, P. J. Org. Lett. 2003, 5, 3641.
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    • García, C.1    Walsh, P.2
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    • For a discussion of the advantages of arylboronic acids in 1,2-addition reactions regarding functional group tolerance, see: Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 343, 343.
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    • For the asymmetric addition of arylzinc reagents, generated in situ from arylboronic acids and diethylzinc to acetophenones, see: (a) Prieto, O.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2003, 14, 1955.
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    • For a comprehensive mechanistic rationale of the rhodium-catalyzed arylboronic acid conjugate addition to enones and a discussion of the crucial role of the protic source in the catalytic activity, see: Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
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    • note
    • A ligand/rhodium ratio of 3/1 gave the optimum enantioselectivity. Using a lower ratio, the ee decreases slightly. This is probably due to competitive chelating properties of both substrate 1 and product 3. Using a higher ratio, dramatically lower activity was observed.
  • 59
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    • and the discussion in the Supporting Information
    • Ligand (S)-L provided product (S)-3a. For determination of the absolute configuration of compound 3a, see: Barroso, S.; Blay, G.; Cardona, L.; Fernandez, I.; Garcia, B.; Pedro, J. R. J. Org. Chem. 2004, 69, 6821 and the discussion in the Supporting Information.
    • (2004) J. Org. Chem. , vol.69 , pp. 6821
    • Barroso, S.1    Blay, G.2    Cardona, L.3    Fernandez, I.4    Garcia, B.5    Pedro, J.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.