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Volumn 38, Issue 13-14, 1999, Pages 2012-2014

Regio- and enantioselective cyclization of epoxy alcohols catalyzed by a [Co(III)(salen)] complex

Author keywords

Asymmetric catalysis; Desymmetrization; Enantiomeric resolution; Heterocycles

Indexed keywords

ALCOHOL DERIVATIVE; COBALT COMPLEX; EPOXIDE;

EID: 0033549570     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990712)38:13/14<2012::AID-ANIE2012>3.0.CO;2-H     Document Type: Article
Times cited : (107)

References (24)
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    • For nitrogen nucleophiles, see L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898; for oxygen nucleophiles, see E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776; M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; for sulfur nucleophiles, see M. H. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252-5254.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 773-776
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    • For nitrogen nucleophiles, see L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898; for oxygen nucleophiles, see E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776; M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; for sulfur nucleophiles, see M. H. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252-5254.
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    • For nitrogen nucleophiles, see L. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898; for oxygen nucleophiles, see E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776; M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938; for sulfur nucleophiles, see M. H. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252-5254.
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    • note
    • The absolute configuration of the products in Table 1 are assigned by analogy to the hydrolytic kinetic resolution also catalyzed by 1, where the (R,R)-catalyst reacts selectively with the S enantiomer of the epoxide reagent.
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    • a) For endo-selective cyclizations promoted by a catalytic antibody, see K. D. Janda, C. G. Shelvin, R. A. Lemer, Science 1993, 259, 490-493;
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    • note
    • For the synthesis of epoxides 2, 3, and 7-10, see the supporting information.
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    • note
    • GC analysis of the reaction showed only 50% conversion of 9 into product.
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    • note
    • The boronic ester derived from phenyl boronic acid is unstable to aqueous workup and chromatography, thus requiring an immobilized version of this ester.
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    • For a mechanistic study of the Cr-catalyzed ARO that indicates a cooperative participation of two metal centers, see K. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.