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Volumn , Issue 22, 2008, Pages 3834-3844

Synthesis of α2,2,β3-diamino acids by double stereodifferentiation aldol addition of oxazolidinone enolates to N-(tert-butylsulfinyl) imines

Author keywords

Amino acids; Antifungal agents; Diastereoselectivity; Nitrogen heterocycles; Oxygen heterocycles; Peptidomimetics

Indexed keywords


EID: 53749100965     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800356     Document Type: Article
Times cited : (9)

References (58)
  • 10
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    • For a summary review of the existing literature, see ref.[1b] For selected references, see: a K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844;
    • For a summary review of the existing literature, see ref.[1b] For selected references, see: a) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844;
  • 24
    • 4143050401 scopus 로고    scopus 로고
    • For reviews on sulfinamides, see: a
    • For reviews on sulfinamides, see: a) P. Zhou, B.-C. Chen, F. A. Davis, Tetrahedron 2004, 60, 8003-8030;
    • (2004) Tetrahedron , vol.60 , pp. 8003-8030
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 26
  • 47
    • 53749091474 scopus 로고    scopus 로고
    • The reaction of lithium enolate (R)-8 (1.0 equiv.) and N-(tertbutoxycarbonyl) benzenemethanimine (1.5 equiv.) obtained in situ from the corresponding carbamoyl sulfone at -80 °C in THF/HMPA (85:15) yielded an inseparable 2.8:1 mixture of two compounds whose structures have not yet been clarified. A. Battaglia, unpublished results.
    • The reaction of lithium enolate (R)-8 (1.0 equiv.) and N-(tertbutoxycarbonyl) benzenemethanimine (1.5 equiv.) obtained in situ from the corresponding carbamoyl sulfone at -80 °C in THF/HMPA (85:15) yielded an inseparable 2.8:1 mixture of two compounds whose structures have not yet been clarified. A. Battaglia, unpublished results.
  • 48
    • 33750436897 scopus 로고    scopus 로고
    • For recent applications of our protocol, see: a
    • For recent applications of our protocol, see: a) A. Guerrini, G. Varchi, A. Battaglia, J. Org. Chem. 2006, 71, 6785-6795;
    • (2006) J. Org. Chem , vol.71 , pp. 6785-6795
    • Guerrini, A.1    Varchi, G.2    Battaglia, A.3
  • 55
    • 53749091734 scopus 로고    scopus 로고
    • This approach is probably preferred to avoid any repulsion of the (R)-configured anomeric hydrogen atom of the rigid sugar moiety with the methyl substituent of the enolate. In this approach, this hydrogen points towards the plane of the enolate
    • This approach is probably preferred to avoid any repulsion of the (R)-configured anomeric hydrogen atom of the rigid sugar moiety with the methyl substituent of the enolate. In this approach, this hydrogen points towards the plane of the enolate.
  • 56
    • 0001222924 scopus 로고
    • S. Knapp, Chem. Rev. 1995, 95, 1859-1876.
    • (1995) Chem. Rev , vol.95 , pp. 1859-1876
    • Knapp, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.