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Volumn 64, Issue 11, 1999, Pages 3830-3837

Origins of regio- and stereoselectivity in acid-promoted reactions of α-lactams

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM;

EID: 0033612359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981734l     Document Type: Article
Times cited : (18)

References (42)
  • 4
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    • Sheehan, J. C.; Lengyel, I. J. Am. Chem. Soc. 1964, 86, 1356-1359. See also a discussion of data from Fuerholzer, J. J., Ph.D. Dissertation, University of Nebraska, 1965, found in ref 1.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1356-1359
    • Sheehan, J.C.1    Lengyel, I.2
  • 6
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    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 767-771
    • Coutts, I.G.C.1    Southcott, M.R.2
  • 7
    • 0344915138 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 43-47
    • Scrimin, P.1    Cavicchioni, G.2    D'Angeli, F.3    Goldblum, A.4    Maran, F.5
  • 8
    • 0005794105 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1985) J. Org. Chem. , vol.50 , pp. 5507-5512
    • Baumgarten, H.E.1    Chaing, N.-C.R.2    Elia, V.J.3    Beum, P.V.4
  • 9
    • 37049103830 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1982) J. Chem. Soc., Chem. Commun. , pp. 1402-1404
    • Bladon, C.M.1    Kirby, G.M.2
  • 10
    • 37049097332 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2969-2972
    • Cavicchioni, G.1    Scrimin, P.2    Veronese, A.C.3    Balboni, G.4    D'Angeli, F.5
  • 11
    • 37049101737 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1980) J. Chem. Soc., Perkin Trans. 1 , pp. 2249-2263
    • Zanotti, G.1    Felira, F.2    Del Pra, A.3    Cavicchioni, G.4    Veronese, A.C.5    D'Angeli, F.6
  • 12
    • 0345346342 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1976) J. Org. Chem. , vol.41 , pp. 3798-3805
    • Baumgarten, H.E.1    McMahan, D.G.2    Elia, V.J.3    Gold, B.I.4    Day, V.W.5    Day, R.O.6
  • 13
    • 0345346345 scopus 로고
    • Work on α-lactams since the Sheehan review, ref 1, until 1990 includes: (a) Coutts, I. G. C.; Southcott, M. R. J. Chem. Soc., Perkin Trans. 1 1990, 767-771. (b) Scrimin, P.; Cavicchioni, G.; D'Angeli, F.; Goldblum, A.; Maran, F. J. Chem. Soc., Perkin Trans. 1 1988, 43-47. (c) Baumgarten, H. E.; Chaing, N.-C. R.; Elia, V. J.; Beum, P. V. J. Org. Chem. 1985, 50, 5507-5512. (d) Bladon, C. M.; Kirby, G. M. J. Chem. Soc., Chem. Commun. 1982, 1402-1404. (e) Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972. (f) Zanotti, G.; Felira, F.; Del Pra, A.; Cavicchioni, G.; Veronese, A. C.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1980, 2249-2263. (g) Baumgarten, H. E.; McMahan, D. G.; Elia, V. J.; Gold, B. I.; Day, V. W.; Day, R. O. J. Org. Chem. 1976, 41, 3798-3805. (h) Talaty, E. R.; Dypuy, A. E., Jr.; Utermoehlen, C. M.; Stekoll, L. H. J. Chem. Soc., Chem. Commun. 1973, 48-49.
    • (1973) J. Chem. Soc., Chem. Commun. , pp. 48-49
    • Talaty, E.R.1    Dypuy A.E., Jr.2    Utermoehlen, C.M.3    Stekoll, L.H.4
  • 29
  • 37
    • 0344052635 scopus 로고    scopus 로고
    • note
    • Rearrangement of the O-protonated species 18 was not examined since an analogous rearrangement would lead to an O-protonated ketenimine oxide, which would likely open directly to species such as 21.
  • 38
    • 0003349349 scopus 로고
    • This interaction is reminiscent of the interaction between the breaking a bond and the σ* orbital of the leaving group which controls the relative rates of reactions of epimers in the concerted solvolysis/ disrotatory ring openings of cyclopropyl derivatives to allyl cations. See, for example: Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 396-397. Schleyer, P. v. R.; Van Dine, G. W.; Schöllkopf, U.; Paust, J. J. Am. Chem. Soc. 1966, 88, 2868-2869.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 396-397
    • Woodward, R.B.1    Hoffmann, R.2
  • 39
    • 0000317126 scopus 로고
    • This interaction is reminiscent of the interaction between the breaking a bond and the σ* orbital of the leaving group which controls the relative rates of reactions of epimers in the concerted solvolysis/ disrotatory ring openings of cyclopropyl derivatives to allyl cations. See, for example: Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 396-397. Schleyer, P. v. R.; Van Dine, G. W.; Schöllkopf, U.; Paust, J. J. Am. Chem. Soc. 1966, 88, 2868-2869.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2868-2869
    • Schleyer, P.V.R.1    Van Dine, G.W.2    Schöllkopf, U.3    Paust, J.4
  • 40
    • 0000541688 scopus 로고    scopus 로고
    • For leading references see: (a) Fabian, W. M. F.; Bakulev, V. A.; Kappe, C. O. J. Org. Chem. 1998, 63, 5801-5805. (b) Birney, D. M.; Ham, S.; Unruh, G. R. J. Am. Chem. Soc. 1997, 119, 4509-4517.
    • (1998) J. Org. Chem. , vol.63 , pp. 5801-5805
    • Fabian, W.M.F.1    Bakulev, V.A.2    Kappe, C.O.3
  • 41
    • 0030978884 scopus 로고    scopus 로고
    • For leading references see: (a) Fabian, W. M. F.; Bakulev, V. A.; Kappe, C. O. J. Org. Chem. 1998, 63, 5801-5805. (b) Birney, D. M.; Ham, S.; Unruh, G. R. J. Am. Chem. Soc. 1997, 119, 4509-4517.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4509-4517
    • Birney, D.M.1    Ham, S.2    Unruh, G.R.3
  • 42
    • 0344915129 scopus 로고    scopus 로고
    • note
    • Optimizations at the B3LYP/6-31G(d) level led to a true transition state for frontside attack. The activation energy for backside attack was estimated from a series of constrained optimizations in which the forming O-C bond length was varied from 1.45 to 2.85 Å.


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