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Volumn 14, Issue 2, 2013, Pages 191-194

Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase

Author keywords

Biocatalysis; Catalytic promiscuity; Michael addition; Nitroaldehydes; Tautomerases

Indexed keywords

4 OXALOCROTONATE TAUTOMERASE; ACETALDEHYDE; ALDEHYDE; ORGANIC SOLVENT; PROLINE; STYRENE; UNCLASSIFIED DRUG;

EID: 84872549328     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200676     Document Type: Article
Times cited : (35)

References (48)
  • 1
    • 77956197277 scopus 로고    scopus 로고
    • and references therein;
    • T. Tokoroyama, Eur. J. Org. Chem. 2010, 2009-2016 and references therein;
    • (2010) Eur. J. Org. Chem. , pp. 2009-2016
    • Tokoroyama, T.1
  • 4
    • 84872546028 scopus 로고    scopus 로고
    • For selected reviews, see:
    • For selected reviews, see:
  • 14
    • 84872555371 scopus 로고    scopus 로고
    • The first organocatalyst for Michael-type additions of unmodified aldehydes to nitroolefins was reported in:
    • The first organocatalyst for Michael-type additions of unmodified aldehydes to nitroolefins was reported in:
  • 15
    • 0035891780 scopus 로고    scopus 로고
    • For a collection of papers in the extensive field of organocatalytic Michael-type addition reactions of aldehydes to nitroolefins see references in:
    • J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740. For a collection of papers in the extensive field of organocatalytic Michael-type addition reactions of aldehydes to nitroolefins see references in:
    • (2001) Org. Lett. , vol.3 , pp. 3737-3740
    • Betancort, J.M.1    Barbas III, C.F.2
  • 20
    • 84872592003 scopus 로고    scopus 로고
    • Some selected examples of asymmetric Michael-type addition reactions of aldehydes to nitroolefins in water:
    • Some selected examples of asymmetric Michael-type addition reactions of aldehydes to nitroolefins in water:
  • 26
    • 84872573349 scopus 로고    scopus 로고
    • Examples of asymmetric Michael-type addition reactions of acetaldehyde to nitroolefins in organic solvents:
    • Examples of asymmetric Michael-type addition reactions of acetaldehyde to nitroolefins in organic solvents:
  • 32
    • 84872555246 scopus 로고    scopus 로고
    • Reference 6b reports the only example of an asymmetric Michael-type addition reaction between acetaldehyde and a nitroolefin (nitrostyrene) in water that we have found in the literature: 10 mol% of organocatalyst yielded 13% of Michael addition product after 18 h of reaction time. This methodology does not include any other aldehyde donor.
    • Reference 6b reports the only example of an asymmetric Michael-type addition reaction between acetaldehyde and a nitroolefin (nitrostyrene) in water that we have found in the literature: 10 mol% of organocatalyst yielded 13% of Michael addition product after 18 h of reaction time. This methodology does not include any other aldehyde donor.
  • 44
    • 0028810542 scopus 로고
    • Synthetic 4-OT was purchased from GenScript USA Inc. (Piscataway, NY). For folding of chemically synthesized 4-OT into active homohexamer see
    • Synthetic 4-OT was purchased from GenScript USA Inc. (Piscataway, NY). For folding of chemically synthesized 4-OT into active homohexamer see: M. C. Fitzgerald, I. Chernushevich, K. G. Standing, S. B. H. Kent, C. P. Whitman, J. Am. Chem. Soc. 1995, 117, 11075-11080.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11075-11080
    • Fitzgerald, M.C.1    Chernushevich, I.2    Standing, K.G.3    Kent, S.B.H.4    Whitman, C.P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.