Highly diastereoselective addition of cyclic β-enamino esters to N-acryloyl-(S)-proline derivatives

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 421-424

  Hervouet, Katia ^a   Guingant, André ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030065771     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00023-7     Document Type: Article

References (24)

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3. For other examples of acid-promoted conjugate addition reactions of chiral β-enaminoesters to electrophilic olefins, see: Bohlmann, C.; Bohlmann, R.; Rivera, E.G.; Vogel, C.; Manandhar, M.D.; Winterfeldt, E. Liebigs Ann. Chem. 1985, 1752-1763. Brunner, H.; Kraus, J.; Lautenschlager, H-J. Monatshefte für Chemie, 1988, 119, 1161-1167.
4. For other examples of acid-promoted conjugate addition reactions of chiral β-enaminoesters to electrophilic olefins, see: Bohlmann, C.; Bohlmann, R.; Rivera, E.G.; Vogel, C.; Manandhar, M.D.; Winterfeldt, E. Liebigs Ann. Chem. 1985, 1752-1763. Brunner, H.; Kraus, J.; Lautenschlager, H-J. Monatshefte für Chemie, 1988, 119, 1161-1167.
5. Sevin, A.; Tortajada, J.; Pfau, M. J. Org. Chem. 1986, 51, 2671-267 . Sevin, A.; Masure, D., Giessner-Prettre, C.; Pfau, M. Helv. Chim. Acta 1990, 73, 552-573
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8. For reviews, see: d'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron Asymmetry, 1992, 3, 459-505 . d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends in Org. Chem. 1993, 4, 555-616.
9. For reviews, see: d'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron Asymmetry, 1992, 3, 459-505 . d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends in Org. Chem. 1993, 4, 555-616.
10. (a) Ramachandran, J.; Li, C.H. J. Org. Chem. 1963, 28, 173-177.
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13. This compound was previously shown to react with cyclopentadiene and other dienes to give the corresponding Diels Alder cycloadducts in good to excellent stereoselectivities. See ref. 7b and the following ones : (a) Waldmann, H. Liebigs Ann. Chem. 1990, 671-680.
14. (b) Waldmann, H.; Dräger, M. Liebigs Ann. Chem. 1990, 681-685. See also, for a recent example of asymmetric 1,3-dipolar cycloaddition involving acrylamide 6a : Waldmann, H.; Bläser, E.; Jansen, M.; Letschert, H.P. Angew. Chem. Int. Ed. Engl. 1993, 115, 683-685.
15. (b) Waldmann, H.; Dräger, M. Liebigs Ann. Chem. 1990, 681-685. See also, for a recent example of asymmetric 1,3-dipolar cycloaddition involving acrylamide 6a : Waldmann, H.; Bläser, E.; Jansen, M.; Letschert, H.P. Angew. Chem. Int. Ed. Engl. 1993, 115, 683-685.
16. Attempts to conduct the reaction in the absence of a Lewis acid or under high pressure activation (up to 12 kbar) failed to provide any evidence of adducts 7 and 8.
17. 1H NMR in the presence of Eu(fod)3.
18. Some rare examples of reactions showing this behaviour were previously reported. See, Markó, I.E; Chesney, A; Hollinshead, D.M.Tetrahedron: Asymmetry, 1994,5, 569-572 and references cited therein.
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21. 3.
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24. It is worth noting that the alternative compact quasi-boat transition state would have led to the opposite (S) configuration at the quaternary carbon centre of 9.