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Volumn , Issue 8, 2003, Pages 1500-1526

Asymmetric synthesis of protected β-substituted and β,β-disubstituted β-amino acids bearing branched hydroxyalkyl side chains and of protected 1,3-amino alcohols with three contiguous stereogenic centers from allylic sulfoximines and aldehydes

Author keywords

Amino acids; Amino alcohols; Asymmetric synthesis

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; AMINO ACID; AMINOALCOHOL; BETA AMINO ACID; ISOBUTYRALDEHYDE; LITHIUM SALT;

EID: 0038032728     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390210     Document Type: Article
Times cited : (52)

References (161)
  • 40
    • 0037124920 scopus 로고    scopus 로고
    • [4o] H. M. L. Davies, C. Venkataramani, Angew. Chem. 2002, 114, 2301; Angew. Chem. Int. Ed. 2002, 41, 2197.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2197
  • 64
    • 0033690703 scopus 로고    scopus 로고
    • For the asymmetric synthesis of acyclic γ-unsubstituted δ-hydroxy-α,β-unsaturated esters through vinylogous aldol reaction, see for example: [8a] G. Casiraghim, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929. [8b] G. Bluet, B. Bazán-Tejeda, J.-M. Campagne, Org. Lett. 2001, 3, 3807. [8c] G. Bluet, J.-M. Campagne, J. Org. Chem. 2001, 66, 4293. [8d] D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654.
    • (2000) Chem. Rev. , vol.100 , pp. 1929
    • Casiraghim, G.1    Zanardi, F.2    Appendino, G.3    Rassu, G.4
  • 65
    • 18044399640 scopus 로고    scopus 로고
    • For the asymmetric synthesis of acyclic γ-unsubstituted δ-hydroxy-α,β-unsaturated esters through vinylogous aldol reaction, see for example: [8a] G. Casiraghim, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929. [8b] G. Bluet, B. Bazán-Tejeda, J.-M. Campagne, Org. Lett. 2001, 3, 3807. [8c] G. Bluet, J.-M. Campagne, J. Org. Chem. 2001, 66, 4293. [8d] D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654.
    • (2001) Org. Lett. , vol.3 , pp. 3807
    • Bluet, G.1    Bazán-Tejeda, B.2    Campagne, J.-M.3
  • 66
    • 0035874694 scopus 로고    scopus 로고
    • For the asymmetric synthesis of acyclic γ-unsubstituted δ-hydroxy-α,β-unsaturated esters through vinylogous aldol reaction, see for example: [8a] G. Casiraghim, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929. [8b] G. Bluet, B. Bazán-Tejeda, J.-M. Campagne, Org. Lett. 2001, 3, 3807. [8c] G. Bluet, J.-M. Campagne, J. Org. Chem. 2001, 66, 4293. [8d] D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654.
    • (2001) J. Org. Chem. , vol.66 , pp. 4293
    • Bluet, G.1    Campagne, J.-M.2
  • 67
    • 0037157166 scopus 로고    scopus 로고
    • For the asymmetric synthesis of acyclic γ-unsubstituted δ-hydroxy-α,β-unsaturated esters through vinylogous aldol reaction, see for example: [8a] G. Casiraghim, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929. [8b] G. Bluet, B. Bazán-Tejeda, J.-M. Campagne, Org. Lett. 2001, 3, 3807. [8c] G. Bluet, J.-M. Campagne, J. Org. Chem. 2001, 66, 4293. [8d] D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5654
    • Evans, D.A.1    Hu, E.2    Burch, J.D.3    Jaeschke, G.4
  • 68
    • 0033575430 scopus 로고    scopus 로고
    • For the asymmetric synthesis of γ-substituted δ-hydroxy-α,β-unsaturated esters through ring opening of diene expoxide esters, see for example: [9a] N. Abe, H. Hanawa, K. Maruoka, M. Sasaki, M. Miyashita, Tetrahedron Lett. 1999, 40, 5369. [9b] Y. Noguchi, T. Yamada, H. Uchiro, S. Kobayashi, Tetrahedron Lett. 2000, 41, 7493.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5369
    • Abe, N.1    Hanawa, H.2    Maruoka, K.3    Sasaki, M.4    Miyashita, M.5
  • 69
    • 0034706368 scopus 로고    scopus 로고
    • For the asymmetric synthesis of γ-substituted δ-hydroxy-α,β-unsaturated esters through ring opening of diene expoxide esters, see for example: [9a] N. Abe, H. Hanawa, K. Maruoka, M. Sasaki, M. Miyashita, Tetrahedron Lett. 1999, 40, 5369. [9b] Y. Noguchi, T. Yamada, H. Uchiro, S. Kobayashi, Tetrahedron Lett. 2000, 41, 7493.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7493
    • Noguchi, Y.1    Yamada, T.2    Uchiro, H.3    Kobayashi, S.4
  • 76
    • 84985534995 scopus 로고
    • [11b] V. Jäger, W. Schwab, V. Buss, Angew. Chem. 1981, 93, 573; Angew. Chem. Int. Ed. Engl. 1981, 20, 601.
    • (1981) Angew. Chem. Int. Ed. Engl. , vol.20 , pp. 601
  • 98
    • 0004005458 scopus 로고
    • (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart
    • For reviews, see: [14a] Stereoselective Synthesis; Houben-Weyl, Methods of Organic Chemistry (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, vol. E 21a.
    • (1995) Stereoselective Synthesis; Houben-Weyl, Methods of Organic Chemistry , vol.E21A
  • 101
    • 0038106171 scopus 로고    scopus 로고
    • [14d] R. Bloch, Chem. Rev. 1998, 98, 1407.
    • (1998) Chem. Rev. , vol.98 , pp. 1407
    • Bloch, R.1
  • 132
  • 133
    • 0038349618 scopus 로고    scopus 로고
    • PhD Thesis, RWTH Aachen
    • R. Loo, PhD Thesis, RWTH Aachen 1999.
    • (1999)
    • Loo, R.1
  • 140
    • 0038349615 scopus 로고    scopus 로고
    • note
    • Cyclization of the trichloroacetyl carbamates in the presence of bases with formation of the corresponding N-trichloroacetyl oxazinones could not be achieved.
  • 142
    • 0038011570 scopus 로고    scopus 로고
    • note
    • Occasionally the cyclization of the carbamates with nBuLi was accompanied to a minor extent by decomposition with formation of the corresponding allylic sulfoximine.
  • 144
    • 84985554917 scopus 로고
    • [33a] H.-J. Gais, I. Erdelmeier, H. J. Lindner, J. Vollhardt, Angew. Chem. 1986, 98, 914; Angew. Chem. Int. Ed. Engl. 1986, 25, 938.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 938
  • 159
    • 0004106636 scopus 로고    scopus 로고
    • (Eds.: S. R. Hall, D. J. du Boulay, R. Olthof-Hazekamp), Universities of Western Australia and Maryland, Lamb, Perth
    • (Eds.: S. R. Hall, D. J. du Boulay, R. Olthof-Hazekamp), XTAL 3.7 System, Universities of Western Australia and Maryland, Lamb, Perth, 2000.
    • (2000) Xtal 3.7 System
  • 160
    • 0004283578 scopus 로고
    • Universität Freiburg, Germany
    • E. Keller, SCHAKAL 92, Universität Freiburg, Germany, 1992.
    • (1992) SCHAKAL 92
    • Keller, E.1
  • 161
    • 0037673649 scopus 로고    scopus 로고
    • note
    • CCDC 191348-191354 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB 2 1EZ (UK); Fax: (internat.) +44-1-223-336-033; or deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.