Stereoselective additions of Grignard reagents to masked imines and iminium ions

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8729-8732

  Bortolussi, Michel ^a   Cinquin, Christophe ^a   Bloch, Robert ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINOALCOHOL; IMINE; ORGANOMETALLIC COMPOUND;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030602159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02013-8     Document Type: Article

References (17)

1. 1. For recent reviews see: a) Johansson, A. Contemporary Organic Synthesis 1995, 2, 393-407.
2. b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
3. c) Volkmann, R.A. in Comprehensive Organic Synthesis, S.L. Schreiber, Ed.; Pergamon Press, Oxford, 1991, Vol. 1, p. 355-396.
4. d) Kleinmann, E.F.; Volkmann, R.A. in Comprehensive Organic Synthesis, C.H. Heatchock Ed.; Pergamon Press, Oxford, 1991, Vol. 2, p. 975-1006.
5. 2. To our knowledge only two studies dealing with the reaction of organometallic reagents with similar hemiaminals (derived from sugars) have been recently reported : a) Nagai, M.; Gaudino, J.J.; Wilcox, C.S. Synthesis 1992, 163-168.
6. b) Cipolla, L.; Lay, L.; Nicotra, F.; Pangrazio, L.; Panza, L. Tetrahedron 1995, 51, 4679-4690.
7. 3. a) Bloch, R.; Gilbert, L. Tetrahedron Lett. 1987, 28, 423-426.
8. b) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605.
9. c) Bloch, R.; Brillet, C. Tetrahedron: Asymmetry 1991, 2, 797-800.
10. 4. Andres, J.M.; Barrio, R.; Martinez, M.A.; Pedrosa, R.; Perez-Encabo, A. J. Org. Chem. 1996, 61, 4210-4213.
11. 5. a) Ref. 2a.
12. b) Berrien, J.F.; Royer, J.; Husson, H.P. J. Org. Chem. 1994, 59, 3769-3774.
13. 6. Hoffmann, R.W. Chem. Rev. 1989, 89, 1841-1860.
14. 7. Chelated transition states have been often postulated to explain the sense of stereoselective additions of organometallics reagents to alkoxy imines. See for example : a) Lay, L.; Nicotra, F.; Paganini, A.; Pangrazio, C.; Panza, L. Tetrahedron Lett. 1993, 34, 4555-4558.
15. b) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083-1092.
16. c) Veith, U.; Leurs, S.; Jäger, V. J. Chem. Soc. Chem. Commun. 1996, 329-330.
17. 8. Microwave irradiations have been made in collaboration with Dr A. Loupy.