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Volumn 6, Issue 13, 2004, Pages 2253-2256

Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; SILANE DERIVATIVE;

EID: 3142759422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049213+     Document Type: Article
Times cited : (173)

References (41)
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    • For recent reports on catalytic hydrogenation (with Ir, Rh, and Ru), see refs 4b-d and the following: (a) Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425. (b) Jiang, X. B.; Minnaard, A. J.; Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de Vries, J. G. Org. Lett. 2003, 5, 1503. (c) Cobley, C. J.; Henschke, J. P. Adv. Synth. Catal. 2003, 345, 195. (d) Okuda, J.; Verch, S.; Stürmer, R.; Spaniol, T. S. J. Organomet. Chem. 2000, 605, 55. For Ru-catalyzed transfer hydrogenation, see: (e) Samec, J. S. M.; Bäckvall, J. E. Chem. Eur. J. 2002, 8, 2955.
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    • note
    • 3 was <5%, and ∼10% in MeCN.
  • 33
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    • Note that chloroform has been shown to be the solvent that most strongly stabilizes the arene-arene interactions: Breault, G. A.; Hunter, C. A.; Mayers, P. C. J. Am. Chem. Soc. 1998, 120, 3402.
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    • note
    • While imines 1a-e,g,h,j,k all exists as pure (E)-isomers, NMR spectra of 1f,i,l indicate 11:1, 14:1, and 3:1 (E/Z)-mixtures, respectively.
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    • This strategy is commonly used in design of chiral selectors in chiral chromatography: Pirkle, W. H.; Koscho, M. E. J. Chromatogr. A 1999, 840, 151.
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    • note
    • 11b
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    • note
    • 18 would dictate the formation of a different transition state, which may result in lower enantioselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.