Highly stereoselective induction in the cobalt-mediated [2+2+2] cycloaddition of chiral phosphine oxides substituted linear enediynes

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5849-5852

  Slowinski, Franck ^a   Aubert, Corinne ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Cobalt and compounds; Cyclisation; Diastereoselection; Diynes

Indexed keywords

COBALT; PHOSPHINE OXIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01137-5     Document Type: Article

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27. 3. For 2a (83%): see (+)-N, N'-Bis[(R)-1-phenylethyl]-1,2-ethylendiamine Horner, L.; Dickerhof, K. Liebigs Ann. Chem. 1984, 1240-1257. For 2b (94%): see N, N'-dimethyl-1,2-diphenylethane-1,2-diamine Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Synthesis in press. For 2c (28%) see Cooper, D.B.; Hall, C. R.; Harrison, J. M.; Inch, T. D. J. Chem. Soc. Perkin Trans. I 1977, 1969-1980. For 2d (66%) : see Korpiun, O.; Lewis, R. A.; Chickos, J. Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846. For 2e (86%) : Crofts, P. C.; Parker, D. M. J. Chem. Soc. (C) 1970, 332-335.
28. 3. For 2a (83%): see (+)-N, N'-Bis[(R)-1-phenylethyl]-1,2-ethylendiamine Horner, L.; Dickerhof, K. Liebigs Ann. Chem. 1984, 1240-1257. For 2b (94%): see N, N'-dimethyl-1,2-diphenylethane-1,2-diamine Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Synthesis in press. For 2c (28%) see Cooper, D.B.; Hall, C. R.; Harrison, J. M.; Inch, T. D. J. Chem. Soc. Perkin Trans. I 1977, 1969-1980. For 2d (66%) : see Korpiun, O.; Lewis, R. A.; Chickos, J. Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846. For 2e (86%) : Crofts, P. C.; Parker, D. M. J. Chem. Soc. (C) 1970, 332-335.
29. 3. For 2a (83%): see (+)-N, N'-Bis[(R)-1-phenylethyl]-1,2-ethylendiamine Horner, L.; Dickerhof, K. Liebigs Ann. Chem. 1984, 1240-1257. For 2b (94%): see N, N'-dimethyl-1,2-diphenylethane-1,2-diamine Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Synthesis in press. For 2c (28%) see Cooper, D.B.; Hall, C. R.; Harrison, J. M.; Inch, T. D. J. Chem. Soc. Perkin Trans. I 1977, 1969-1980. For 2d (66%) : see Korpiun, O.; Lewis, R. A.; Chickos, J. Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846. For 2e (86%) : Crofts, P. C.; Parker, D. M. J. Chem. Soc. (C) 1970, 332-335.
30. 3. For 2a (83%): see (+)-N, N'-Bis[(R)-1-phenylethyl]-1,2-ethylendiamine Horner, L.; Dickerhof, K. Liebigs Ann. Chem. 1984, 1240-1257. For 2b (94%): see N, N'-dimethyl-1,2-diphenylethane-1,2-diamine Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Synthesis in press. For 2c (28%) see Cooper, D.B.; Hall, C. R.; Harrison, J. M.; Inch, T. D. J. Chem. Soc. Perkin Trans. I 1977, 1969-1980. For 2d (66%) : see Korpiun, O.; Lewis, R. A.; Chickos, J. Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846. For 2e (86%) : Crofts, P. C.; Parker, D. M. J. Chem. Soc. (C) 1970, 332-335.
31. 3. For 2a (83%): see (+)-N, N'-Bis[(R)-1-phenylethyl]-1,2-ethylendiamine Horner, L.; Dickerhof, K. Liebigs Ann. Chem. 1984, 1240-1257. For 2b (94%): see N, N'-dimethyl-1,2-diphenylethane-1,2-diamine Alexakis, A.; Aujard, I.; Kanger, T.; Mangeney, P. Organic Synthesis in press. For 2c (28%) see Cooper, D.B.; Hall, C. R.; Harrison, J. M.; Inch, T. D. J. Chem. Soc. Perkin Trans. I 1977, 1969-1980. For 2d (66%) : see Korpiun, O.; Lewis, R. A.; Chickos, J. Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846. For 2e (86%) : Crofts, P. C.; Parker, D. M. J. Chem. Soc. (C) 1970, 332-335.
32. 36OPCo: C, 66.97 ; H, 8.43. Found: C, 66.89 ; H, 8.49.