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Volumn 11, Issue 20, 2009, Pages 4648-4651

Invertible enantioselectivity in 6′-deoxy-6′-acylamino-β- isocupreidine-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction: Key role of achiral additive

Author keywords

[No Author keywords available]

Indexed keywords

6' HYDROXYCINCHONIDINE; 6'-HYDROXYCINCHONIDINE; AMIDE; DRUG DERIVATIVE; QUININE; QUINOLINE DERIVATIVE; QUINUCLIDINE DERIVATIVE;

EID: 70349934416     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901920s     Document Type: Article
Times cited : (71)

References (90)
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  • 15
    • 0041878745 scopus 로고    scopus 로고
    • β-ICD was used as an efficient catalyst in other reactions
    • (f) France, S.; Guerin. D. J.; Miller, S. J.: Lectka, T. Chem. Rev. 2003, 103, 2985β-ICD was used as an efficient catalyst in other reactions.
    • (2003) Chem. Rev. , vol.103 , pp. 2985
    • France, S.1    Guerin, D.J.2    Miller, S.J.3    Lectka, T.4
  • 47
    • 56749164602 scopus 로고    scopus 로고
    • The effect of the orthohydroxy group on enantiodivergent phosphoric acid-catalyzed Povarov reaction has also been reported
    • Shi and co-workers have recently reported a substrate-directed reversal of enantioselectivity by using salicyl N-tosylimines. (a) Shi, M.; Qi, M.-J.; Liu, X.-G. Chem. Commun. 2008, 6025. The effect of the orthohydroxy group on enantiodivergent phosphoric acid-catalyzed Povarov reaction has also been reported. See:
    • (2008) Chem. Commun. , pp. 6025
    • Shi, M.1    Qi, M.-J.2    Liu, X.-G.3
  • 50
    • 70349920872 scopus 로고    scopus 로고
    • la-catalyzed reaction between 3a and MVK leading to (R)-adduct in 85% yield and 97% ee in DMF-MeCN. See ref 5.
    • la-catalyzed reaction between 3a and MVK leading to (R)-adduct in 85% yield and 97% ee in DMF-MeCN. See ref 5.
  • 56
    • 17844379719 scopus 로고    scopus 로고
    • Achiral additives reverse the enantioselectivity. For reviews, see: (a) Sibi, M. P.: Liu, M. Curr. Org. Chem. 2001, 5, 719.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 719
    • Sibi, M.P.1    Liu, M.2
  • 58
    • 56249102432 scopus 로고    scopus 로고
    • For selected examples
    • (c) Tanaka. T.: Hayashi, M. Synthesis 2008, 3361. For selected examples, see:
    • (2008) Synthesis , pp. 3361
    • Tanaka, T.1    Hayashi, M.2
  • 86
    • 0037048346 scopus 로고    scopus 로고
    • Matched/mismatched enantioselective MBH and aza-MBH reaction, see: (a) Shi, M.; Jiang, J.-K. Tetrahedron: Asymmetry 2002, 13, 1941.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1941
    • Shi, M.1    Jiang, J.-K.2
  • 88
    • 34948840851 scopus 로고    scopus 로고
    • Effect of achiral additive on the yield and ee of aza-MBH reaction has been reported. See for examples: (a) Shi, Y.-L.; Shi, M. Adv. Synth. Catal. 2007, 349, 2129. See also:
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 2129
    • Shi, Y.-L.1    Shi, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.