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Volumn 74, Issue 7, 2009, Pages 2798-2803

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-α-alkyl β-amino esters

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; ASYMMETRIC SYNTHESIS; GOOD YIELDS; SULFINIMINES;

EID: 64249134238     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9001504     Document Type: Article
Times cited : (19)

References (44)
  • 1
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    • For a review, see: a
    • For a review, see: (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
    • (2002) Tetrahedron , vol.58 , pp. 7991
    • Liu, M.1    Sibi, M.P.2
  • 3
    • 57149097169 scopus 로고    scopus 로고
    • For recent reviews on β-peptides, see
    • (a) For recent reviews on β-peptides, see: Seebach, D; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366.
    • (2008) Acc. Chem. Res , vol.41 , pp. 1366
    • Seebach, D.1    Gardiner, J.2
  • 6
    • 33747113614 scopus 로고    scopus 로고
    • For reviews of sulfinimine chemistry which also include discussions of β-amino acid syntheses, see: a
    • For reviews of sulfinimine chemistry which also include discussions of β-amino acid syntheses, see: (a) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
    • (2006) Tetrahedron , vol.62 , pp. 8869
    • Morton, D.1    Stockman, R.A.2
  • 11
    • 34250824031 scopus 로고    scopus 로고
    • For the application of sulfinimines in the asymmetric synthesis of α-alkyl-amino acids, see: a
    • For the application of sulfinimines in the asymmetric synthesis of α-alkyl-amino acids, see: (a) Davis, F. A.; Song, M. Org. Lett. 2007, 9, 2413.
    • (2007) Org. Lett , vol.9 , pp. 2413
    • Davis, F.A.1    Song, M.2
  • 14
    • 0037366617 scopus 로고    scopus 로고
    • For a review on the Morita-Baylis-Hillman reaction, see
    • For a review on the Morita-Baylis-Hillman reaction, see: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
    • (2003) Chem. Rev , vol.103 , pp. 811
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 15
    • 34247582194 scopus 로고    scopus 로고
    • Thermal elimination of benzenesulfenic acid from α- phenylsulfinylmethyl-β-(N-sulfinylamino) esters is reported to give α-methylene-β-(N-sulfinyamino) esters. See: Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Undo, H. J. Org. Chem. 2007, 72, 3569.
    • Thermal elimination of benzenesulfenic acid from α- phenylsulfinylmethyl-β-(N-sulfinylamino) esters is reported to give α-methylene-β-(N-sulfinyamino) esters. See: Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Undo, H. J. Org. Chem. 2007, 72, 3569.
  • 32
    • 84869266741 scopus 로고    scopus 로고
    • 3N, and DMAP (79%). See Experimental Section.
    • 3N, and DMAP (79%). See Experimental Section.
  • 34
    • 0033396486 scopus 로고    scopus 로고
    • For leading references to the asymmetric synthesis of anti-α-substituted β-amino esters via the α-alkylation of β-amino esters dianions, see: (a) Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553. See also:
    • For leading references to the asymmetric synthesis of anti-α-substituted β-amino esters via the α-alkylation of β-amino esters dianions, see: (a) Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553. See also:
  • 36
    • 37049071174 scopus 로고    scopus 로고
    • For other methods for the asymmetric synthesis of anti-α- substituted β-amino esters, see: (a) Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129.
    • For other methods for the asymmetric synthesis of anti-α- substituted β-amino esters, see: (a) Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129.
  • 39
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    • Ref 5c
    • (d) Ref 5c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.