Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis

Tetrahedron Asymmetry

Volumn 13, Issue 23, 2002, Pages 2619-2624

  Couty, François ^a   Prim, Damien ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL; AZETIDINE DERIVATIVE; DIETHYLZINC; KETONE DERIVATIVE; LITHIUM DERIVATIVE; PHENYLLITHIUM; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG; ZINC BROMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0037180574     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00710-3     Document Type: Article

References (16)

1. (a) Rodebaugh R.M., Cromwell N.H. J. Heterocycl. Chem. 1971, 421-430;
2. (b) Kulkarni S.B., Cromwell N.H. J. Heterocycl. Chem. 1977, 981-983;
3. (c) Arnould J.C., Cossy J., Pete J.P. Tetrahedron. 1980, 36, 1585-1592.
4. Agami C., Couty F., Evano G. Tetrahedron: Asymmetry. 13:2002;297-302.
5. Soai K., Niwa S. Chem. Rev. 1992;833-856.
6. Enders D., Shilvock J.P. Chem. Soc. Rev. 29:2000;359.
7. Bruylants P. Bull. Soc. Chem. Belg. 33:1924;467.
8. The signal for the C-2 proton in these ketones appears systematically more shielded to an amount of ca. 1 ppm in 2,3-trans-isomers compared to the cis-isomers due to the field effect of the α-phenyl substituent. See Section 3.
9. Besev M., Engman L. Org. Lett. 4:2002;3023-3025.
10. N-Debenzylation of alcohol 17a failed in our hands. This is the reason why we turned to the synthesis of an N-allyl azetidine.
11. Upon screening of different bases and solvents, the described conditions were found to be the best for minimizing the amount of diallylation.
12. Alcaide B., Almendros P., Alonso J.M., Aly M.F. Org. Lett. 3:2001;3781-3784.
13. For previously reported use of azetidinic amino alcohols in this reaction, see: (a) Behnen, W.; Mehler, T.; Martens, J.; Tetrahedron: Asymmetry 1993, 4, 1413-1416; (b) Shi, M.; Jiang, J. K. Tetrahedron: Asymmetry 1999, 10, 1673-1679; (c) Wilken, J.; Erny, S.; Wassman, S.; Martens, J. Tetrahedron: Asymmetry 2000, 11, 2143-2148; (d) Hermsen, P. J.; Cremers, J. G. O.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 2001, 42, 4243-4245.
14. For previously reported use of azetidinic amino alcohols in this reaction, see: (a) Behnen, W.; Mehler, T.; Martens, J.; Tetrahedron: Asymmetry 1993, 4, 1413-1416; (b) Shi, M.; Jiang, J. K. Tetrahedron: Asymmetry 1999, 10, 1673-1679; (c) Wilken, J.; Erny, S.; Wassman, S.; Martens, J. Tetrahedron: Asymmetry 2000, 11, 2143-2148; (d) Hermsen, P. J.; Cremers, J. G. O.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 2001, 42, 4243-4245.
15. For previously reported use of azetidinic amino alcohols in this reaction, see: (a) Behnen, W.; Mehler, T.; Martens, J.; Tetrahedron: Asymmetry 1993, 4, 1413-1416; (b) Shi, M.; Jiang, J. K. Tetrahedron: Asymmetry 1999, 10, 1673-1679; (c) Wilken, J.; Erny, S.; Wassman, S.; Martens, J. Tetrahedron: Asymmetry 2000, 11, 2143-2148; (d) Hermsen, P. J.; Cremers, J. G. O.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 2001, 42, 4243-4245.
16. For previously reported use of azetidinic amino alcohols in this reaction, see: (a) Behnen, W.; Mehler, T.; Martens, J.; Tetrahedron: Asymmetry 1993, 4, 1413-1416; (b) Shi, M.; Jiang, J. K. Tetrahedron: Asymmetry 1999, 10, 1673-1679; (c) Wilken, J.; Erny, S.; Wassman, S.; Martens, J. Tetrahedron: Asymmetry 2000, 11, 2143-2148; (d) Hermsen, P. J.; Cremers, J. G. O.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 2001, 42, 4243-4245.