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Volumn 43, Issue 52, 2002, Pages 9625-9628

Palladium-catalyzed hydrocarbonation of methyleneaziridines with carbon pronucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBON; PALLADIUM;

EID: 0037164674     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02410-3     Document Type: Article
Times cited : (23)

References (40)
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • 0035929109 scopus 로고    scopus 로고
    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
    • (2001) Chem. Commun. , pp. 1784
    • Hayes, J.F.1    Shipman, M.2    Twin, H.3
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    • 0037039889 scopus 로고    scopus 로고
    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • Hayes, J.F.1    Shipman, M.2    Twin, H.3
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    • 0030820798 scopus 로고    scopus 로고
    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5887
    • Ince, J.1    Shipman, M.2    Ennis, D.S.3
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
    • (2000) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2047
    • Ennis, D.S.1    Ince, J.2    Rahman, S.3    Shipman, M.4
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 1462
    • Bottini, A.T.1    Roberts, J.D.2
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
    • (1975) J. Org. Chem. , vol.40 , pp. 2045
    • Crandall, J.K.1    Crawley, L.C.2    Komin, J.B.3
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • Bottini, A.T.1    Roberts, J.D.2
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    • 0011932847 scopus 로고
    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • Jongejan, E.1    Steinberg, H.2    De Boer, T.3
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    • For ring-opening reactions of methyleneaziridines, see: (a) Quast, H.; Weise Velez, C. A. Angew. Chem., Int. Ed. Engl. 1974, 13, 342; (b) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2000, 1791; (c) Hayes, J. F.; Shipman, M.; Twin, H. Chem. Commun. 2001, 1784; (d) Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935; (e) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887; (f) Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047; (g) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1957, 79, 1462; (h) Crandall, J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045; (i) Bottini, A. T.; Roberts, J. D. J. Am. Chem. Soc. 1962, 84, 195; (j) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1978, 97, 146; (k) Jongejan, E.; Steinberg, H.; De Boer, T. J. Recl. Trav. Chim. Pays-Bas. 1979, 98, 66.
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    • 3, is also conceivable.
    • 3, is also conceivable.
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    • Pd-catalyzed ring-expansion reactions of methyleneaziridine with carbon monoxide: Pd(0) catalyst inserts into N-C2 bond of methyleneaziridines. See:
    • Pd-catalyzed ring-expansion reactions of methyleneaziridine with carbon monoxide: Pd(0) catalyst inserts into N-C2 bond of methyleneaziridines. See: Alper H., Hamel N. Tetrahedron Lett. 28:1987;3237.
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
    • (1996) Tetrahedron , vol.52 , pp. 7037
    • Ince, J.1    Ross, T.M.2    Shipman, M.3    Slawin, A.M.Z.4    Ennis, D.S.5
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 3397
    • Ince, J.1    Ross, T.M.2    Shipman, M.3    Ennis, D.S.4
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    • For the preparation of 2-methyleneaziridines, see: (a) Pollard, C. B.; Parcell, R. F. J. Am. Chem. Soc. 1951, 73, 2925; (b) Bingham, E. M.; Gilbert, C. J. J. Org. Chem. 1975, 40, 224; (c) Atkinson, R. S.; Malpass, J. R. Tetrahedron Lett. 1975, 4305; (d) Ince, J.; Ross, T. M.; Shipman, M.; Slawin, A. M. Z.; Ennis, D. S. Tetrahedron 1996, 52, 7037; (e) Ince, J.; Ross, T. M.; Shipman, M.; Ennis, D. S. Tetrahedron: Asymmetry 1996, 7, 3397; (f) De Kimpe, N.; De Smaele, D; Skonyi, Z. J. Org. Chem. 1997, 62, 2448.
    • (1997) J. Org. Chem. , vol.62 , pp. 2448
    • De Kimpe, N.1    De Smaele, D.2    Skonyi, Z.3


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