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Volumn 11, Issue 8, 2009, Pages 1828-1831

Erratum: Correction to Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chirally Modified AZADOs (Organic Letters (2009) 11:8 (1829-1831) DOI: 10.1021/ol900441f);Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

Author keywords

[No Author keywords available]

Indexed keywords

2 AZAADAMANTANE N OXYL; 2-AZAADAMANTANE N-OXYL; ADAMANTANE; ALCOHOL DERIVATIVE; AMINE OXIDE; DRUG DERIVATIVE;

EID: 65249189478     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502543r     Document Type: Erratum
Times cited : (62)

References (32)
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    • For reviews on the preparation of optically active alcohols, see: a, John Wiley & Sons: New York
    • For reviews on the preparation of optically active alcohols, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York. 1994.
    • (1994) Asymmetric Catalysis in Organic Synthesis
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    • Kagan. H. B.; Flaud. J.'c. Kinetic Resolution. Tov. Stereochem. 1988, 18, 249-330.
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    • For selective examples of chiral nitroxyl-radical-catalyzed OKR, see:(a) Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem. 1993, 58, 4837-4843.
    • For selective examples of chiral nitroxyl-radical-catalyzed OKR, see:(a) Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem. 1993, 58, 4837-4843.
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    • For examples of cation-π interaction, see: (a) Kawabata. T; Nagato. M, Takasu, K, Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170
    • For examples of cation-π interaction, see: (a) Kawabata. T; Nagato. M.: Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170.
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    • An interesting paper, in which the effects on the jr-facial diastereo- selectivity of the substituent in the 4-position of adamantin-2-one were investigated, has been reported; see:(a) Barboni, L, Filippi, A, Fraschetti, C; Giuli, S, Marcolini, M, Marcantoni. E. Tetrahedron Lett. 2008, 49, 6065-6067
    • An interesting paper, in which the effects on the jr-facial diastereo- selectivity of the substituent in the 4-position of adamantin-2-one were investigated, has been reported; see:(a) Barboni, L.; Filippi, A.; Fraschetti, C; Giuli, S.; Marcolini, M.; Marcantoni. E. Tetrahedron Lett. 2008, 49, 6065-6067.
  • 21
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    • s values for OKR. In view of its availability, we chose the chiral AZADOH catalyst for further study.
    • s values for OKR. In view of its availability, we chose the chiral AZADOH catalyst for further study.
  • 22
    • 65249132836 scopus 로고    scopus 로고
    • See Supporting Information for details of the preparation of the catalysts and screening for reaction conditions in OKR
    • See Supporting Information for details of the preparation of the catalysts and screening for reaction conditions in OKR.
  • 25
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    • s values, see; (a) Kagan, H. B.; Flaud, J. C. In Topics in Stereochemistry; Eliel. E. L., Ed.; Wiley & Sons: New York. 1988; 18. pp 249-330. (b) Vedejs, E.; Jure, M. Angew. Client., Int. Ed. 2005, 44, 3974-4001.
    • s values, see; (a) Kagan, H. B.; Flaud, J. C. In Topics in Stereochemistry; Eliel. E. L., Ed.; Wiley & Sons: New York. 1988; Vol. 18. pp 249-330. (b) Vedejs, E.; Jure, M. Angew. Client., Int. Ed. 2005, 44, 3974-4001.
  • 26
    • 65249104758 scopus 로고    scopus 로고
    • The sterically congested z'-Pr group of the catalyst decreased catalytic activity and enantioselectivity. We consider that flexibility of the substituent group as normal butyl group is essential for the generation of broad asymmetric reaction space. This assumption was supported by the fact that catalyst 2 with a Me group gave low selectivity with other secondary alcohols (see Supporting Information).
    • The sterically congested z'-Pr group of the catalyst decreased catalytic activity and enantioselectivity. We consider that flexibility of the substituent group as normal butyl group is essential for the generation of broad asymmetric reaction space. This assumption was supported by the fact that catalyst 2 with a Me group gave low selectivity with other secondary alcohols (see Supporting Information).
  • 27
    • 0000149447 scopus 로고    scopus 로고
    • Optically active 2-substituted cyclohexanols and cyclohexane diol derivatives are reliable tools as chiral reagents, especially as auxiliaries, for asymmetric synthesis; see: (a) Whitesell, J. K. Chem. Rev. 1992, 92, 953-964.
    • Optically active 2-substituted cyclohexanols and cyclohexane diol derivatives are reliable tools as chiral reagents, especially as auxiliaries, for asymmetric synthesis; see: (a) Whitesell, J. K. Chem. Rev. 1992, 92, 953-964.
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    • Tanyeli, C; Turkut, E.; Akhmedov, I. M. Tetrahedron: Asymmetry- 2004, 15, 1729-1733.
    • (e) Tanyeli, C; Turkut, E.; Akhmedov, I. M. Tetrahedron: Asymmetry- 2004, 15, 1729-1733.
  • 32
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    • rel < 4) and with rapid oxidation rate, indicating that substituent size at C-1 of chiral AZADO plays essential roles for the efficient resolution.
    • rel < 4) and with rapid oxidation rate, indicating that substituent size at C-1 of chiral AZADO plays essential roles for the efficient resolution.


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