메뉴 건너뛰기




Volumn 59, Issue 3, 2003, Pages 341-352

Stereoselective routes to substituted β-amino carbonyl compounds via heterodiene [4π+2π] cycloadditions of auxiliary-based C2 symmetric ketene acetals

Author keywords

amino acid; Chiral auxiliary; Heterodiene cycloaddition; Ketene acetal; Pyrano 4,3 b pyridine

Indexed keywords

ACETAL DERIVATIVE; ALKADIENE; BETA AMINO ACID; CARBONYL DERIVATIVE;

EID: 0037434029     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01523-5     Document Type: Article
Times cited : (14)

References (44)
  • 1
    • 0000293463 scopus 로고
    • For reviews, see: (a) Desimoni G., Tacconi G. Chem. Rev. 75:1975;651-692 (b) Boger D.L., Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis. 1987;Academic, London. pp 167-213.
    • (1975) Chem. Rev. , vol.75 , pp. 651-692
    • Desimoni, G.1    Tacconi, G.2
  • 7
    • 0002497398 scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1994) Aldrichim. Acta , vol.27 , pp. 3-11
    • Juaristi, E.1    Quintana, D.2    Escalante, J.3
  • 8
    • 0028130028 scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 9
    • 14844312173 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1996) Chem. Soc. Rev. , vol.25 , pp. 117-128
    • Cardillo, G.1    Tomasini, C.2
  • 10
    • 0003693460 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1997) Enantioselective Synthesis of Beta-Aminoacids
    • Tang, T.P.1    Ellman, J.A.2
  • 11
    • 0012354067 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1999) J. Org. Chem. , vol.64 , pp. 12-13
    • Evans, D.A.1    Wu, L.D.2    Wiener, J.J.M.3    Johnson, J.S.4    Ripin, D.H.B.5    Tedrow, J.S.6
  • 12
    • 0012350659 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1999) J. Org. Chem. , vol.64 , pp. 6411-6417
    • Roche, D.1    Prasad, K.2    Repic, O.3
  • 13
    • 0012305653 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3665-3668
    • Kawakami, T.1    Ohtake, H.2    Arakawa, H.3    Okachi, T.4    Imada, Y.5    Murahashi, S.-I.6
  • 14
    • 0012353223 scopus 로고    scopus 로고
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1999) Org. Lett. , vol.1 , pp. 107-110
    • Miyabe, H.1    Fujii, K.2    Naito, T.3
  • 15
    • 0000227151 scopus 로고    scopus 로고
    • For reviews, see (a). E. Juaristi. New York: Wiley. For recent examples, see (e)
    • For reviews, see (a) Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3-11 (b) Cole D.C. Tetrahedron. 50:1994;9517-9582 (c) Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128 (d) Juaristi E. Enantioselective Synthesis of Beta-Aminoacids. 1997;Wiley, New York. For recent examples, see (e) Tang T.P., Ellman J.A. J. Org. Chem. 64:1999;12-13 (f) Evans D.A., Wu L.D., Wiener J.J.M., Johnson J.S., Ripin D.H.B., Tedrow J.S. J. Org. Chem. 64:1999;6411-6417 (g) Roche D., Prasad K., Repic O. Tetrahedron Lett. 40:1999;3665-3668 (h) Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110 (i) Miyabe H., Fujii K., Naito T. Org. Lett. 1:1999;569-572.
    • (1999) Org. Lett. , vol.1 , pp. 569-572
  • 16
    • 0033709712 scopus 로고    scopus 로고
    • For a review of stereoselective piperidine synthesis, see
    • For a review of stereoselective piperidine synthesis, see Laschat S., Dickner T. Synthesis. 2000;1781-1813.
    • (2000) Synthesis , pp. 1781-1813
    • Laschat, S.1    Dickner, T.2
  • 17
    • 0022993068 scopus 로고
    • For examples and leading references, see (a) Tietze L.F., Voss E. Tetrahedron Lett. 27:1986;6181-6184 (b) Tietze L.F., Hartfiel U. Tetrahedron Lett. 31:1990;1697-1700. (c) See also De Gaudenzi L., Apparao S., Schmidt R.R. Tetrahedron. 46:1990;277-290. and references cited therein.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 6181-6184
    • Tietze, L.F.1    Voss, E.2
  • 18
    • 0025238871 scopus 로고
    • For examples and leading references, see (a) Tietze L.F., Voss E. Tetrahedron Lett. 27:1986;6181-6184 (b) Tietze L.F., Hartfiel U. Tetrahedron Lett. 31:1990;1697-1700. (c) See also De Gaudenzi L., Apparao S., Schmidt R.R. Tetrahedron. 46:1990;277-290. and references cited therein.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1697-1700
    • Tietze, L.F.1    Hartfiel, U.2
  • 19
    • 0001713216 scopus 로고
    • For examples and leading references, see (a). (c) See also. and references cited therein
    • For examples and leading references, see (a) Tietze L.F., Voss E. Tetrahedron Lett. 27:1986;6181-6184 (b) Tietze L.F., Hartfiel U. Tetrahedron Lett. 31:1990;1697-1700. (c) See also De Gaudenzi L., Apparao S., Schmidt R.R. Tetrahedron. 46:1990;277-290. and references cited therein.
    • (1990) Tetrahedron , vol.46 , pp. 277-290
    • De Gaudenzi, L.1    Apparao, S.2    Schmidt, R.R.3
  • 23
    • 0025878767 scopus 로고
    • For an alternative approach to this objective, see (a)
    • For an alternative approach to this objective, see (a) Sato M., Kitazawa N., Nagashima S., Kaneko C., Inoue N., Furuya T. Tetrahedron. 47:1991;7271-7278 (b) Sato M., Kitazawa N., Nagashima S., Kano K., Kaneko C. Chem. Lett. 1992;485-488.
    • (1992) Chem. Lett. , pp. 485-488
    • Sato, M.1    Kitazawa, N.2    Nagashima, S.3    Kano, K.4    Kaneko, C.5
  • 24
    • 0034728950 scopus 로고    scopus 로고
    • For a preliminary account of some of this work, see
    • For a preliminary account of some of this work, see Ray C.A., Wallace T.W., Ward R.A. Tetrahedron Lett. 41:2000;3501-3504.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3501-3504
    • Ray, C.A.1    Wallace, T.W.2    Ward, R.A.3
  • 30
    • 0001635878 scopus 로고
    • For the exploitation of this hydrolytic process as a route to diol monoacetates, see:
    • For the exploitation of this hydrolytic process as a route to diol monoacetates, see: Zhu P.C., Lin J., Pittman C.U. J. Org. Chem. 60:1995;5729-5931.
    • (1995) J. Org. Chem. , vol.60 , pp. 5729-5931
    • Zhu, P.C.1    Lin, J.2    Pittman, C.U.3
  • 38
    • 0012256583 scopus 로고    scopus 로고
    • The various conformations of 12 containing s-cis enone units were generated using Quantum CAChe 4.5 (Fujitsu) and their geometries optimised using an augmented MM3 force field. The results suggest that the hydrogen-bonded arrangement depicted for 12 in Figure 2 is 4.9 kcal/mol lower in energy than the closest alternative
    • The various conformations of 12 containing s-cis enone units were generated using Quantum CAChe 4.5 (Fujitsu) and their geometries optimised using an augmented MM3 force field. The results suggest that the hydrogen-bonded arrangement depicted for 12 in Figure 2 is 4.9 kcal/mol lower in energy than the closest alternative.
  • 41
    • 0012341594 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for compound 20 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 192457. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk)
    • Crystallographic data (excluding structure factors) for compound 20 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 192457. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 43
    • 0012354428 scopus 로고    scopus 로고
    • 1H NMR spectrum of this sample was identical to that of a sample of (±)-36, supplied by Dr A. P. Flynn, Mereside Laboratories, AstraZeneca
    • 1H NMR spectrum of this sample was identical to that of a sample of (±)-36, supplied by Dr A. P. Flynn, Mereside Laboratories, AstraZeneca.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.