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Volumn 46, Issue 42, 2010, Pages 8040-8042

One-pot sequential alcohol oxidation and asymmetric α-oxyamination in aqueous media using recyclable resin-supported peptide catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PEPTIDE; RESIN;

EID: 77958460966     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc02301a     Document Type: Article
Times cited : (41)

References (53)
  • 42
    • 34247165162 scopus 로고    scopus 로고
    • Originally, the catalytic process was considered to include the oxidation of the enamine intermediate by a metal reagent. Recently, MacMillan et al. published the paper posing a question for the mechanism proposed by Sibi;
    • M. P. Sibi M. Hasegawa J. Am. Chem. Soc. 2007 129 4124
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 4124
    • Sibi, M.P.1    Hasegawa, M.2
  • 51
    • 0028925665 scopus 로고
    • The amounts of carboxylic acid 5 generated in the α-oxyamination of an aldehyde and the tandem reaction of an alcohol under different reaction conditions are described in the supplementary information When (5R)-(+)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride (Aldrich 663069) was used instead of peptide catalyst 1, 3a was obtained in 28% yield and 66% ee For a review, see
    • T. Inokuchi K. Nakagawa S. Torii Tetrahedron Lett. 1995 36 3223
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3223
    • Inokuchi, T.1    Nakagawa, K.2    Torii, S.3
  • 52
    • 47749137879 scopus 로고    scopus 로고
    • The resin catalyst was filtered off and washed after each cycle of the reuse. Gravimetric analysis of the dried resin indicated that 0 to 80% of copper-bipyridine complex remained inside the resin. The fairly broad range in the amount of the residual copper complex might be due to the difference in washing conditions. In the reuse of the peptide catalyst, the copper salt and bipyridine were added in order to ensure the reproducibility regardless of the way of washing For example, when cerium(iv) ammonium nitrate, a much stronger oxidizing agent than a copper salt, was employed for the asymmetric α-oxyamination of an aldehyde, recycling peptide catalyst 1 drastically decreased yield and enantioselectivity. In case of 2a, the reaction gave the product with 71% yield and 89% ee in the first reuse of 1, but with 14% yield and 58% ee in the second reuse During the revision of this manuscript, Maruoka et al.
    • M. Gruttadauria F. Giacalone R. Noto Chem. Soc. Rev. 2008 37 1666
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1666
    • Gruttadauria, M.1    Giacalone, F.2    Noto, R.3
  • 53
    • 77956551916 scopus 로고    scopus 로고
    • 10.1002/anie.201002965. This paper also includes the one-pot reaction from an alcohol. However, it is not a tandem-type method, but an orthogonal one in which reagents are added sequentially
    • T. Kano H. Mii K. Maruoka Angew. Chem., Int. Ed. 2010 49 6638 10.1002/anie.201002965
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6638
    • Kano, T.1    Mii, H.2    Maruoka, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.