메뉴 건너뛰기




Volumn , Issue 14, 2007, Pages 1421-1423

A reductase-mimicking thiourea organocatalyst incorporating a covalently bound NADH analogue: Efficient 1,2-diketone reduction with in situ prosthetic group generation and recycling

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE; OXIDOREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; THIOUREA DERIVATIVE;

EID: 33947668980     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b618792g     Document Type: Article
Times cited : (60)

References (72)
  • 63
    • 33644771025 scopus 로고    scopus 로고
    • Only one metal-based system has been reported to promote highly enantioselective asymmetric transfer hydrogenation of 1,2-diketones (benzil not tested):
    • D. Menche J. Hassfeld J. Li G. Menche A. Ritter S. Rudolf Org. Lett. 2006 8 741
    • (2006) Org. Lett. , vol.8 , pp. 741
    • Menche, D.1    Hassfeld, J.2    Li, J.3    Menche, G.4    Ritter, A.5    Rudolf, S.6
  • 64
    • 0034736377 scopus 로고    scopus 로고
    • For a report on the difficulties associated with mono-reduction of benzils, see:
    • T. Koike K. Murata T. Ikariya Org. Lett. 2000 2 3833
    • (2000) Org. Lett. , vol.2 , pp. 3833
    • Koike, T.1    Murata, K.2    Ikariya, T.3
  • 65
    • 0000759992 scopus 로고    scopus 로고
    • For a very recent example of metal-catalysed enantioselective reductions of α-keto esters using stoichiometric loadings of a Hanztsch dihydropyridine, see:
    • K. Murata K. Okano M. Miyagi H. Iwane R. Noyori T. Ikariya Org. Lett. 1999 1 1119
    • (1999) Org. Lett. , vol.1 , pp. 1119
    • Murata, K.1    Okano, K.2    Miyagi, M.3    Iwane, H.4    Noyori, R.5    Ikariya, T.6
  • 66
    • 33845993240 scopus 로고    scopus 로고
    • 4 requires 3-4 equiv. of reductant and reflux temperatures in aqueous media:
    • J. W. Yang B. List Org. Lett. 2006 8 5653
    • (2006) Org. Lett. , vol.8 , pp. 5653
    • Yang, J.W.1    List, B.2
  • 69
    • 33947689859 scopus 로고    scopus 로고
    • Reductions involving these catalysts (and the control reaction) were clean/chemoselective: no diols or other side products were detected
    • Reductions involving these catalysts (and the control reaction) were clean/chemoselective: no diols or other side products were detected
  • 70
    • 33947656062 scopus 로고    scopus 로고
    • Highly activated substrates such as aceanthrenequinone, 1-phenyl-1,2-propanedione and methylphenylglyoxylate underwent fast reduction in the absence of catalyst This level of stereoinduction was reproducible over several experiments. When this reaction was repeated under the conditions used in Table 2 we detected (somewhat counter-intuitively) only racemic 2 at both 5 and 75% conversion
    • Highly activated substrates such as aceanthrenequinone, 1-phenyl-1,2-propanedione and methylphenylglyoxylate underwent fast reduction in the absence of catalyst
  • 71
    • 33947676504 scopus 로고    scopus 로고
    • 1 kg of sodium dithionite costs Stg £17.60 (Aldrich catalogue) Note added in proof: after the original submission of this manuscript, a report concerning the efficient recycling of BNA in the ring-opening reduction of chalcone oxide appeared, see:
    • 1 kg of sodium dithionite costs Stg £17.60 (Aldrich catalogue)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.