New, readily available organocatalysts for the enantioselective reduction of α-imino- and β-imino esters

Synlett

Volumn , Issue 8, 2011, Pages 1085-1088

  Bonsignore, Martina ^a   Benaglia, Maurizio ^a   Annunziata, Rita ^a   Celentano, Giuseppe ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

imino esters; imines; Lewis base; stereo selective reduction; trichlorosilane

Indexed keywords

ALPHA IMINO ESTER; BETA IMINO ESTER; ENAMINE; ESTER; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 79955877091     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259941     Document Type: Article

References (25)

1. For a recent review on chiral amine synthesis, see:, Nugent T C., El-Shazly M, Adv. Synth. Catal. 2010 352 753
2. For a review on metal-catalyzed hydrogenation of imines, see:, Fleury-Bregeot N, deleFuente V, Castillon S, Claver C, Chem. Catal. Chem. 2010 2 1346
3. Geng H, Zhang W, Chen J, Hou G, Zhou L, Zou Y, Wu W, Zhang X, Angew. Chem. Int. Ed. 2009 48 6052
4. Steinhuebel D, Sun Y, Matsumura K, Sayo N, Saito T, J. Am. Chem. Soc. 2009 131 11316
5. Connon S J., Org. Biomol. Chem. 2007 5 3407
6. Akiyama T, Chem. Rev. 2007 107 5744
7. Terada M, Chem. Commun. 2008 4098
8. Reviews:, Benaglia M, Guizzetti S, Pignataro L, Coord. Chem. Rev. 2008 252 492
9. Denmark S E., Beutner G L., Angew. Chem. Int. Ed. 2008 47 1560
10. 3-mediated reductions, see:, Guizzetti S, Benaglia M, Eur. J. Org. Chem. 2010 5529
11. Iwasaki F, Onomura O, Mishima K, Maki T, Matsumura Y, Tetrahedron Lett. 1999 40 7507
12. Iwasaki F, Onomura O, Mishima K, Kanematsu T, Maki T, Matsumura Y, Tetrahedron Lett. 2001 42 2525
13. Xue Z.-Y, Jiang Y, Yuan W.-C, Zhang X.-M, Eur. J. Org. Chem. 2010 616
14. Guizzetti S, Benaglia M, Rossi S, Org. Lett. 2009 11 2928
15. See also:, Wang C, Wu X, Zhou L, Sun J, Chem. Eur. J. 2008 14 8789
16. For two recent contributions on the enantioselective synthesis of -amino acids involving the use of trichlorosilane, see:, Malkov A V., Stoncius S, Vrankova K, Arndt M, Kocovsky P, Chem. Eur. J. 2008 14 8082
17. Zheng H.-J, Chen W.-B, Wu Z.-J, Deng [nl]J.-G, Lin W.-Q, Yuan W.-C, Zhang X.-M, Chem. Eur. J. 2008 14 9864; and references cited therein
18. For a very recent review on the importance of -amino acids, see:, Weiner B, Szymansky W, Janssen D B., Minaard A J., Feringa B L., Chem. Soc. Rev. 2010 39 1656
19. Guizzetti S, Benaglia M, EP 2008010079 2008, Guizzetti S, Benaglia M, Eur. Patent Appl. EP07023240.0 2008, Guizzetti S, Benaglia M, Cozzi F, Annunziata R, Tetrahedron 2009 65 6354
20. Guizzetti S, Biaggi C, Benaglia M, Celentano G, Synlett 2010 134
21. Guizzetti S, Benaglia M, Bonsignore M, Raimondi L, Celentano G, Org. Biomol. Chem. 2011 9 in press
22. For the diastereoselective reduction of these chiral substrates through hydrogenation with different catalytic systems, see:, Nugent T C., El-Shazly M, Wachaure V N., J. Org. Chem. 2008 73 1297; and references cited therein
23. Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M, Org. Lett. 2005 7 3781
24. Hoffmann S, Seayad A M., List B, Angew. Chem. Int. Ed. 2005 44 7424 See also ref. 2.
25. Li G, Liang Y, Antilla J C., J. Am. Chem. Soc. 2007 129 5830 See also ref. 5.