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Volumn 79, Issue 7, 2014, Pages 3238-3243

Preparation of both C5′ epimers of 5′- C -methyladenosine: Reagent control trumps substrate control

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

EID: 84898064962     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500089t     Document Type: Article
Times cited : (23)

References (51)
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    • 80054726956 scopus 로고    scopus 로고
    • 3P is a registered trademark for propylphosphonic anhydride. For its use with pyridine as a base, see
    • 3P is a registered trademark for propylphosphonic anhydride. For its use with pyridine as a base, see: Dunetz, J. R.; Xiang, Y.; Baldwin, A.; Ringling, J. Org. Lett. 2011, 13, 5048-5051
    • (2011) Org. Lett. , vol.13 , pp. 5048-5051
    • Dunetz, J.R.1    Xiang, Y.2    Baldwin, A.3    Ringling, J.4
  • 21
    • 0016375205 scopus 로고
    • Ketone 5 has been prepared previously by oxidizing the mixed secondary alcohols. See
    • Ketone 5 has been prepared previously by oxidizing the mixed secondary alcohols. See: Ranganathan, R.; Jones, G. H.; Moffatt, J. G. J. Org. Chem. 1974, 39, 290-298
    • (1974) J. Org. Chem. , vol.39 , pp. 290-298
    • Ranganathan, R.1    Jones, G.H.2    Moffatt, J.G.3
  • 37
    • 84865749803 scopus 로고    scopus 로고
    • The reduction of α-phenoxyacetophenone using a Ru(II)-TsDPEN catalyst proceeds with 84.4% ee; however, the absolute stereochemistry of the reduction indicates that the benzene ring of the acetophenone rather than the ether oxygen atom is the predominant control element. See - 2555
    • The reduction of α-phenoxyacetophenone using a Ru(II)-TsDPEN catalyst proceeds with 84.4% ee; however, the absolute stereochemistry of the reduction indicates that the benzene ring of the acetophenone rather than the ether oxygen atom is the predominant control element. See: Jolley, K. E.; Zanotti-Gerosa, A.; Hancock, F.; Dyke, A.; Grainger, D. M.; Medlock, J. A.; Neddon, H. G.; Le Paih, J. J. M.; Roseblade, S. J.; Seger, A.; Sivakumar, V.; Prokes, I.; Morris, D. J.; Wills, M. Adv. Synth. Catal. 2012, 354, 2545-2555
    • (2012) Adv. Synth. Catal. , vol.354 , pp. 2545
    • Jolley, K.E.1    Zanotti-Gerosa, A.2    Hancock, F.3    Dyke, A.4    Grainger, D.M.5    Medlock, J.A.6    Neddon, H.G.7    Le Paih, J.J.M.8    Roseblade, S.J.9    Seger, A.10    Sivakumar, V.11    Prokes, I.12    Morris, D.J.13    Wills, M.14
  • 44
    • 33744491804 scopus 로고    scopus 로고
    • For details, see the Experimental Section. In addition to (R, R)- and (S, S)-TsDPEN, this study also examined camphor-derived (S, S, S)-CsDPEN. See: Li, X.; Blacker, J.; Houson, I.; Wu, X.; Xiao, J. Synlett 2006, 1155-1160
    • (2006) Synlett , pp. 1155-1160
    • Li, X.1    Blacker, J.2    Houson, I.3    Wu, X.4    Xiao, J.5
  • 48
    • 84876270859 scopus 로고    scopus 로고
    • For a review of aromatic interactions as control elements in stereoselective organic reactions, see: Krenske, E. H.; Houk, K. N. Acc. Chem. Res. 2013, 46, 979-989
    • (2013) Acc. Chem. Res. , vol.46 , pp. 979-989
    • Krenske, E.H.1    Houk, K.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.