Stereodivergent Baylis-Hillman reaction of a chiral acryloyl imide exploiting ion-chelation effect: Mechanistic insight on the rearrangement of trichloroacetimidates of the Baylis-Hillman adducts to trichloroacetamides

Monatshefte fur Chemie

Volumn 138, Issue 1, 2007, Pages 27-33

  Marcucci, Eleonora ^a   Martelli, Gianluca ^a   Orena, Mario ^a   Rinaldi, Samuele ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Baylis Hillman; Chelation; Chiral imide; Rearrangement; Stereoselection

Indexed keywords

EID: 33846029090     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-006-0570-5     Document Type: Article

References (26)

1. a) Ciclosi M, Fava C, Galeazzi R, Orena M, Sepulveda-Arques J (2002) Tetrahedron Lett 43: 2199;
2. b) Galeazzi R, Martelli G, Orena M, Rinaldi S (2004) Synthesis 2560
3. a) Fikentscher R, Hahn E, Kud A, Oftring A (1987) Offen DE 3,444,097; (1987) Chem Abstr 107: 7781;
4. b) Brown JM, Rose M, Knight FI, Wienand A (1995) Recl Trav Chim Pays-Bas 114: 242
5. R Galeazzi G Martelli M Orena S Rinaldi 2006 Monatsh Chem 137 357
6. a) Galeazzi R, Martelli G, Mobbili G, Orena M, Rinaldi S (2004) Tetrahedron: Asymmetry 15: 3249;
7. b) Galeazzi R, Martelli G, Orena M, Rinaldi S, Sabatino P (2005) Tetrahedron 61: 5465;
8. c) Galeazzi R, Martelli G, Natali D, Orena M, Rinaldi S (2005) Tetrahedron: Asymmetry 16: 1779
9. a) Orena M, Porzi G, Sandri S (1992) J Chem Res (S) 42;
10. b) Bongini A, Cardillo G, Gentilucci L, Tomasini C (1997) J Org Chem 62: 9148
11. WJ Close 1950 J Org Chem 15 1131
12. a) Cardillo G, D'Amico A, Orena M, Sandri S (1988) J Org Chem 53: 2354;
13. b) Cardillo G, Orena M, Romero M, Sandri S (1989) Tetrahedron 45: 1501;
14. c) Cardillo B, Galeazzi R, Mobbili G, Orena M, Rossetti M (1994) Tetrahedron: Asymmetry 8: 1535
15. a) Kawamura M, Kobayashi S (1999) Tetrahedron Lett 40: 1539;
16. b) Rosa JN, Afonso CAM, Santos AG (2001) Tetrahedron 57: 4189
17. Although we have not experienced any problem in the handling of lithium perchlorate, care should be taken when manipulating it due to its potentially explosive nature. Sax NI Dangerous Properties of Industrial Materials, 5th ed.; Van Nostrand Reinhold Company: New York, 1979
18. It is worth mentioning that the Baylis-Hillman reaction of the imide 3 gives satisfactory results only starting from ethyl glyoxalate 2. In fact even electrophilic aldehydes such as 4-nitrobenzaldehyde and 2,4-dinitrobenzaldehyde failed to give any results, and starting materials were invariably recovered
19. a) Overman LE (1974) J Am Chem Soc 96: 597;
20. b) Overman LE (1976) J Am Chem Soc 98: 2901;
21. c) Mehmandust M, Petit Y, Larchevèque M (1992) Tetrahedron Lett 33: 4313;
22. d) Kang SH, Kim GT, Yoo YS (1997) Tetrahedron Lett 38: 603;
23. e) Martin C, Bortolussi M, Bloch R (1999) Tetrahedron Lett 40: 3735;
24. f) Nishikawa T, Asai M, Ohyabu N, Isobe M (1998) J Org Chem 63: 188;
25. g) Kang SH, Kim JS, Youn JH (1998) Tetrahedron Lett 39: 9047
26. R Amoroso G Cardillo P Sabatino C Tomasini A Treré 1993 J Org Chem 58 5615