메뉴 건너뛰기




Volumn , Issue 8, 2000, Pages 1569-1576

Synthesis and ring opening of methyl 2-alkyl-3-(alkyl/aryl)-1- benzoylaziridine-2-carboxylates: Synthesis of polysubstituted amino acids

Author keywords

Aziridines; Oxazolines; Ring expansion reactions; Hydroxy amino acids; Hydroxy amino acids

Indexed keywords

AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE;

EID: 0034062501     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1569::aid-ejoc1569>3.0.co;2-x     Document Type: Article
Times cited : (37)

References (46)
  • 1
    • 0003416748 scopus 로고
    • Pergamon Press, Oxford
    • For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
    • (1989) Synthesis of Optically Active Amino Acids
    • Williams, R.M.1
  • 2
    • 0028355337 scopus 로고
    • For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
    • (1994) Tetrahedron , vol.50 , pp. 1539-1650
    • Duthaler, R.O.1
  • 3
    • 0003799353 scopus 로고
    • (Ed.: M. Wolff), Wiley and Sons, New York
    • For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
    • (1995) Burger's Medicinal Chemistry and Drug Discovery, 5th Ed. , pp. 803-861
    • Goodman, M.1    Ro, S.2
  • 4
    • 0030768259 scopus 로고    scopus 로고
    • For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
    • (1997) Tetrahedron , vol.53 , pp. 12789-12854
    • Hanessian, S.1    McNaughton-Smith, G.2    Lombart, H.-G.3    Lubell, W.D.4
  • 5
    • 0033583532 scopus 로고    scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1093-1095
    • Panek, J.S.1    Masse, C.E.2
  • 6
    • 0032542772 scopus 로고    scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2330-2336
    • Corey, E.J.1    Li, W.2    Reichard, G.A.3
  • 7
    • 0003106787 scopus 로고    scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1998) Angew. Chem. Int. Ed. , vol.110 , pp. 1784-1787
    • Corey, E.J.1    Li, W.2    Nagamitsu, T.3
  • 8
    • 0001406020 scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2139-2140
    • Uno, H.1    Baldwin, J.E.2    Russell, A.T.3
  • 9
    • 0029995939 scopus 로고    scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3584-3590
    • Nagamitsu, T.1    Sunazuka, T.2    Omura, S.3    Sprengler, P.A.4    Smith A.B. III5
  • 10
    • 0028914644 scopus 로고
    • See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
    • (1995) Chem. Commun. , pp. 793-794
    • Chida, N.1    Takeoka, J.2    Tsutsumi, N.3    Ogawa, S.4
  • 22
    • 0342614616 scopus 로고    scopus 로고
    • A synthesis of benzyl (2S,3R)-N-(benzyloxycarbonyl)-2,3-dimetnylaziridine-2-carboxylate is reported in ref.[5e]
    • A synthesis of benzyl (2S,3R)-N-(benzyloxycarbonyl)-2,3-dimetnylaziridine-2-carboxylate is reported in ref.[5e]
  • 42
    • 85088714491 scopus 로고    scopus 로고
    • 2O, only the starting aziridine was recovered
    • 2O, only the starting aziridine was recovered.
  • 43
    • 0343484637 scopus 로고    scopus 로고
    • As both C2 and C3 positions are not activated for the substitution, the solvent plays a crucial role. In DMF the reaction proceeds with lower yield and requires more Lewis acid than in dichloromethane. In these conditions the C2 attack is favoured, probably owing to the coordinating effect of DMF. Acetonitrile shows an intermediate behaviour, affording a regioisomeric mixture. With 3-phenyl-substituted aziridines (see further) different results are obtained because the phenyl group stabilises the incipient carbocation at C3 and the solvent effect is over-whelmed, so that the C2 attack is never observed
    • As both C2 and C3 positions are not activated for the substitution, the solvent plays a crucial role. In DMF the reaction proceeds with lower yield and requires more Lewis acid than in dichloromethane. In these conditions the C2 attack is favoured, probably owing to the coordinating effect of DMF. Acetonitrile shows an intermediate behaviour, affording a regioisomeric mixture. With 3-phenyl-substituted aziridines (see further) different results are obtained because the phenyl group stabilises the incipient carbocation at C3 and the solvent effect is over-whelmed, so that the C2 attack is never observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.