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Volumn , Issue 6, 2007, Pages 959-964

A one-pot asymmetric sequential animation-alkylation of aldehydes: Expedient synthesis of aliphatic chiral amines

Author keywords

Amines; Cuprates (R) or (S) (methylbenzyl)amine; Enantioenriched amines; In situ aldimine formation

Indexed keywords


EID: 34250657458     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600781     Document Type: Article
Times cited : (12)

References (41)
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    • Scaleup Studies in Asymmetric Transfer Hydrogenation
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    • J. Blacker, J. Martin, "Scaleup Studies in Asymmetric Transfer Hydrogenation" in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions (Eds.: H.-U Blaser, E. Schmidt), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2004, pp. 201-216.
    • (2004) Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions , pp. 201-216
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    • Ellman has demonstrated the advantageous use of (R)- or (S)-tert-butanesulfinamide for aliphatic α-chiral amine synthesis, see: a) G. Liu, D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc. 1997, 119, 9913-9914;
    • Ellman has demonstrated the advantageous use of (R)- or (S)-tert-butanesulfinamide for aliphatic α-chiral amine synthesis, see: a) G. Liu, D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc. 1997, 119, 9913-9914;
  • 18
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    • Charette has recently published a one-pot protocol, see
    • Charette has recently published a one-pot protocol, see: A. Côté, A. B. Charette, J. Org. Chem. 2005, 70, 10864-10867.
    • (2005) J. Org. Chem , vol.70 , pp. 10864-10867
    • Côté, A.1    Charette, A.B.2
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    • For further examples of enantioselective carbanion addition to aliphatic aldimines, see: a
    • For further examples of enantioselective carbanion addition to aliphatic aldimines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878;
    • (2000) J. Org. Chem , vol.65 , pp. 5875-5878
    • Denmark, S.E.1    Stiff, C.M.2
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    • For advances in diastereoselective carbanion addition to (R)-or (S)-N-α-(methylbenzyl) aliphatic aldimine, see: a) G. Alvaro, D. Savoia, M. R. Valentinetti, Tetrahedron 1996, 52, 12571-12586;
    • For advances in diastereoselective carbanion addition to (R)-or (S)-N-α-(methylbenzyl) aliphatic aldimine, see: a) G. Alvaro, D. Savoia, M. R. Valentinetti, Tetrahedron 1996, 52, 12571-12586;
  • 26
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    • For further examples of diastereoselective carbanion addition to chiral imines, see: a
    • For further examples of diastereoselective carbanion addition to chiral imines, see: a) D. Enders, H. Schubert, C. Nübling, Angew. Chem. Int. Ed. Engl. 1986, 25, 1109-1110;
    • (1986) Angew. Chem. Int. Ed. Engl , vol.25 , pp. 1109-1110
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    • [2a,2b,5a].
    • [2a,2b,5a].
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    • [2c].
    • [2c].
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    • [17]
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    • In all instances the major amine diastereomer, S,S-2, could be isolated in analytically pure form by using flash chromatography or by recrystallization of the HCl or HBr salt. An exception to this general rule was noted for amine 2f, which could not be further enriched
    • In all instances the major amine diastereomer, (S,S)-2, could be isolated in analytically pure form by using flash chromatography or by recrystallization of the HCl or HBr salt. An exception to this general rule was noted for amine 2f, which could not be further enriched.
  • 40
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    • [11c], and by extrapolation for compounds 2a, 2b, 2d, 2f, and 2g.
    • [11c], and by extrapolation for compounds 2a, 2b, 2d, 2f, and 2g.
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    • A previous investigation with the corresponding preformed imine resulted in the same de, even though the compounds were added in the reverse order, see ref.[11b
    • [11b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.