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Volumn 10, Issue 16, 1999, Pages 3197-3207

Double diastereoselection in asymmetric [2+3] cycloaddition of chiral oxazoline N-oxides: Application to the kinetic resolution of a racemic α,β-unsaturated δ-lactone

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE; LACTONE; OXAZOLINE DERIVATIVE;

EID: 0033551874     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00317-1     Document Type: Article
Times cited : (39)

References (31)
  • 6
    • 0023620073 scopus 로고
    • Hochuli, E.; Kupfer, E.; Maurer, R.; Meister, W.; Mercadal, Y.; Schmidt, K. J. Antibiot. 1987, 40, 1086. For recent total syntheses: Paterson, I.; Doughty, V. A. Tetrahedron Lett. 1999, 40, 393; Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 2679; Pommier, A.; Pons, J.-M. Synthesis 1995, 729 and references cited therein.
    • (1987) J. Antibiot. , vol.40 , pp. 1086
    • Hochuli, E.1    Kupfer, E.2    Maurer, R.3    Meister, W.4    Mercadal, Y.5    Schmidt, K.6
  • 7
    • 0033534342 scopus 로고    scopus 로고
    • For recent total syntheses:
    • Hochuli, E.; Kupfer, E.; Maurer, R.; Meister, W.; Mercadal, Y.; Schmidt, K. J. Antibiot. 1987, 40, 1086. For recent total syntheses: Paterson, I.; Doughty, V. A. Tetrahedron Lett. 1999, 40, 393; Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 2679; Pommier, A.; Pons, J.-M. Synthesis 1995, 729 and references cited therein.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 393
    • Paterson, I.1    Doughty, V.A.2
  • 8
    • 33748675953 scopus 로고    scopus 로고
    • Hochuli, E.; Kupfer, E.; Maurer, R.; Meister, W.; Mercadal, Y.; Schmidt, K. J. Antibiot. 1987, 40, 1086. For recent total syntheses: Paterson, I.; Doughty, V. A. Tetrahedron Lett. 1999, 40, 393; Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 2679; Pommier, A.; Pons, J.-M. Synthesis 1995, 729 and references cited therein.
    • (1998) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2679
    • Fleming, I.1    Lawrence, N.J.2
  • 9
    • 0029119647 scopus 로고
    • and references cited therein
    • Hochuli, E.; Kupfer, E.; Maurer, R.; Meister, W.; Mercadal, Y.; Schmidt, K. J. Antibiot. 1987, 40, 1086. For recent total syntheses: Paterson, I.; Doughty, V. A. Tetrahedron Lett. 1999, 40, 393; Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 2679; Pommier, A.; Pons, J.-M. Synthesis 1995, 729 and references cited therein.
    • (1995) Synthesis , pp. 729
    • Pommier, A.1    Pons, J.-M.2
  • 10
    • 0005159348 scopus 로고
    • Double diastereoselection was first introduced by Kagan and co-workers:
    • Double diastereoselection was first introduced by Kagan and co-workers: Horeau, A.; Kagan, H. B.; Vigneron, J.-P. Bull. Soc. Chim. Fr. 1968, 3795. For a review, see: Masamune, S.; Choy.; Petersen, J. S. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
    • (1968) Bull. Soc. Chim. Fr. , pp. 3795
    • Horeau, A.1    Kagan, H.B.2    Vigneron, J.-P.3
  • 11
    • 0021775497 scopus 로고
    • For a review, see:
    • Double diastereoselection was first introduced by Kagan and co-workers: Horeau, A.; Kagan, H. B.; Vigneron, J.-P. Bull. Soc. Chim. Fr. 1968, 3795. For a review, see: Masamune, S.; Choy.; Petersen, J. S. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 1
    • Masamune, S.1    Choy2    Petersen, J.S.3
  • 12
    • 0029978168 scopus 로고    scopus 로고
    • Alternative syntheses of 2: (S enantiomer);
    • Alternative syntheses of 2: Raina, S.; Singh, V. K. Tetrahedron 1996, 52, 4479 (S enantiomer); Pohmakotr, M.; Jaruyan, P. Tetrahedron Lett. 1985, 26, 2253 (racemic).
    • (1996) Tetrahedron , vol.52 , pp. 4479
    • Raina, S.1    Singh, V.K.2
  • 13
    • 0011983580 scopus 로고
    • (racemic)
    • Alternative syntheses of 2: Raina, S.; Singh, V. K. Tetrahedron 1996, 52, 4479 (S enantiomer); Pohmakotr, M.; Jaruyan, P. Tetrahedron Lett. 1985, 26, 2253 (racemic).
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2253
    • Pohmakotr, M.1    Jaruyan, P.2
  • 14
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews, see:
    • For recent reviews, see: Grubbs, R. H.; Chang, S.; Tetrahedron 1998, 54, 4413; Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 15
  • 16
    • 0038163433 scopus 로고    scopus 로고
    • Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130; see also: Ghosh, A. K. Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9130
    • Fürstner, A.1    Langemann, K.2
  • 18
    • 0000987495 scopus 로고
    • 2BOMe, as initially described by Brown: Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4763
    • Jadhav, P.K.1
  • 19
    • 0001646391 scopus 로고
    • 2BOMe, as initially described by Brown:
    • 2BOMe, as initially described by Brown: Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
    • (1991) J. Org. Chem. , vol.56 , pp. 401
    • Racherla, U.S.1    Brown, H.C.2
  • 22
    • 0026335244 scopus 로고
    • For examples of kinetic resolutions in [2+3] cycloadditions, see:
    • For examples of kinetic resolutions in [2+3] cycloadditions, see: Gotti, A.; Cicchi, S.; Brandi, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371; Brandi, A.; Cicchi, S.; Gotti, A.; Koprowski, M.; Pietrusiewicz, K. M. J. Org. Chem. 1994, 59, 1315; Katagiri, N.; Okoda, M.; Morishita, Y.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1996, 2137; Gilberston, S. R.; Lopez, O. D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1116.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 1371
    • Gotti, A.1    Cicchi, S.2    Brandi, A.3    Pietrusiewicz, K.M.4
  • 23
    • 0001653621 scopus 로고
    • For examples of kinetic resolutions in [2+3] cycloadditions, see: Gotti, A.; Cicchi, S.; Brandi, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371; Brandi, A.; Cicchi, S.; Gotti, A.; Koprowski, M.; Pietrusiewicz, K. M. J. Org. Chem. 1994, 59, 1315; Katagiri, N.; Okoda, M.; Morishita, Y.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1996, 2137; Gilberston, S. R.; Lopez, O. D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1116.
    • (1994) J. Org. Chem. , vol.59 , pp. 1315
    • Brandi, A.1    Cicchi, S.2    Gotti, A.3    Koprowski, M.4    Pietrusiewicz, K.M.5
  • 24
    • 0002363006 scopus 로고    scopus 로고
    • For examples of kinetic resolutions in [2+3] cycloadditions, see: Gotti, A.; Cicchi, S.; Brandi, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371; Brandi, A.; Cicchi, S.; Gotti, A.; Koprowski, M.; Pietrusiewicz, K. M. J. Org. Chem. 1994, 59, 1315; Katagiri, N.; Okoda, M.; Morishita, Y.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1996, 2137; Gilberston, S. R.; Lopez, O. D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1116.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 2137
    • Katagiri, N.1    Okoda, M.2    Morishita, Y.3    Kaneko, C.4
  • 25
    • 0033583491 scopus 로고    scopus 로고
    • For examples of kinetic resolutions in [2+3] cycloadditions, see: Gotti, A.; Cicchi, S.; Brandi, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371; Brandi, A.; Cicchi, S.; Gotti, A.; Koprowski, M.; Pietrusiewicz, K. M. J. Org. Chem. 1994, 59, 1315; Katagiri, N.; Okoda, M.; Morishita, Y.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1996, 2137; Gilberston, S. R.; Lopez, O. D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1116.
    • (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , pp. 1116
    • Gilberston, S.R.1    Lopez, O.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.