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Volumn 11, Issue 9, 2009, Pages 1959-1962

A Tandem conjugate addition/cyclization protocol for the asymmetric synthesis of 2-Aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID; LITHIUM; ORGANOMETALLIC COMPOUND; QUINOLINE DERIVATIVE;

EID: 65549138086     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9004118     Document Type: Article
Times cited : (41)

References (78)
  • 2
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    • For selected recent synthetic approaches to the Martinelle alkaloids, see: Nyerges, M. Heterocycles 2004, 63, 1685.
    • For selected recent synthetic approaches to the Martinelle alkaloids, see: Nyerges, M. Heterocycles 2004, 63, 1685.
  • 31
    • 0023795586 scopus 로고
    • For instance, see
    • For instance, see: Reed, J. N. Tetrahedron Lett. 1988, 29, 5725.
    • (1988) Tetrahedron Lett , vol.29 , pp. 5725
    • Reed, J.N.1
  • 37
    • 0034681822 scopus 로고    scopus 로고
    • For instance, see
    • For instance, see: Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947.
    • (2000) Tetrahedron Lett , vol.41 , pp. 1947
    • Ma, D.1    Sun, H.2
  • 66
    • 48249099656 scopus 로고    scopus 로고
    • For a related conjugate addition/cyclisation protocol for the synthesis of tetrahydroquinoline derivatives, see: Youn, S. W, Song, J.-H, Jung, D.-I. J. Org. Chem. 2008, 73, 5658
    • For a related conjugate addition/cyclisation protocol for the synthesis of tetrahydroquinoline derivatives, see: Youn, S. W.; Song, J.-H.; Jung, D.-I. J. Org. Chem. 2008, 73, 5658.
  • 68
    • 66149148216 scopus 로고    scopus 로고
    • The condensation of a range of aniline derivatives with a range of aldehydes is known to give the corresponding (ZT)-configured imines with good to excellent levels of diastereoselectivity; see: Tennant, G. Comprehensive Organic Chemistry; Barton, D. E, Ollis, W. D, Eds, Pergamon: Oxford, 1979; 2, Chapter 8. Patai, S. The Chemistry of the Carbon- Nitrogen Double Bond; John Wiley and Sons: Chichester, 1970. For some very recent examples, see: Shen, M, Driver, T. G. Org. Lett. 2008, 10, 3367
    • The condensation of a range of aniline derivatives with a range of aldehydes is known to give the corresponding (ZT)-configured imines with good to excellent levels of diastereoselectivity; see: Tennant, G. Comprehensive Organic Chemistry; Barton, D. E., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, Chapter 8. Patai, S. The Chemistry of the Carbon- Nitrogen Double Bond; John Wiley and Sons: Chichester, 1970. For some very recent examples, see: Shen, M.; Driver, T. G. Org. Lett. 2008, 10, 3367.
  • 70
    • 66149118528 scopus 로고    scopus 로고
    • The parent amine (K)-N-benzyl-N-(a-methylbenzyl)amine was assessed to be >98% ee by 1H NMR chiral shift experiments using (S)- O-acetylmandelic acid and comparison with an authentic racemic sample.
    • The parent amine (K)-N-benzyl-N-(a-methylbenzyl)amine was assessed to be >98% ee by 1H NMR chiral shift experiments using (S)- O-acetylmandelic acid and comparison with an authentic racemic sample.
  • 71
    • 66149094585 scopus 로고    scopus 로고
    • Given the known enantiomeric purity (i.e., >98% ee) of the lithium amide (R)-4 used to initiate the tandem conjugate addition/cyclization process, the enantiomeric purity of 15, 16, and 22-27 was assigned from the diastereoisomeric purity (determined by peak integration of the 1H NMR spectrum of the crude reaction mixture and the pure product).
    • Given the known enantiomeric purity (i.e., >98% ee) of the lithium amide (R)-4 used to initiate the tandem conjugate addition/cyclization process, the enantiomeric purity of 15, 16, and 22-27 was assigned from the diastereoisomeric purity (determined by peak integration of the 1H NMR spectrum of the crude reaction mixture and the pure product).
  • 72
    • 66149140518 scopus 로고    scopus 로고
    • (R)-N-tert-Butoxycarbonyl-N-benzyl-N-(a- methylbenzyl)amine, formed by reaction of the excess lithium amide (R)-4 with (Boc)2O, was also isolated.
    • (R)-N-tert-Butoxycarbonyl-N-benzyl-N-(a- methylbenzyl)amine, formed by reaction of the excess lithium amide (R)-4 with (Boc)2O, was also isolated.
  • 78
    • 66149089097 scopus 로고    scopus 로고
    • The remarkable resistance of, aryl, amino ester derivatives to undergo cleavage of the N-C(3) bond has been attributed to the presence of an intramolecular hydrogen bond between the, amino substituents and the carbonyl oxygen atom that holds the C(3)-aryl group in a conformation that disfavors hydrogenolysis of the benzylic N-C(3) bond; see ref 8a
    • The remarkable resistance of /?-aryl-/?-amino ester derivatives to undergo cleavage of the N-C(3) bond has been attributed to the presence of an intramolecular hydrogen bond between the /?-amino substituents and the carbonyl oxygen atom that holds the C(3)-aryl group in a conformation that disfavors hydrogenolysis of the benzylic N-C(3) bond; see ref 8a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.