Primary amine catalyzed electrophilic amination of α,α- disubstituted aldehydes

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4430-4432

  Desmarchelier, Alaric ^a   Yalgin, Hasret ^a   Coeffard, Vincent ^a   Moreau, Xavier ^a   Greck, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Amination; Branched aldehydes; Organocatalysis; Primary amine; Quaternary stereocenter

Indexed keywords

ALDEHYDE; AMINE;

AMINATION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; ELECTROPHILICITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 79960848137     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.063     Document Type: Article

References (23)

1. T. Vilaivan, and W. Bhanthumnavin Molecules 15 2010 917 958
2. C. Greck, B. Drouillat, and C. Thomassigny Eur. J. Org. Chem. 2004 1377 1385
3. For seminal reports, see: A. Bogevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, and K.A. Jørgensen Angew. Chem., Int. Ed. 41 2002 1790 1793
4. B. List J. Am. Chem. Soc. 124 2002 5656 5657
5. R. Ait-Youcef, D. Kalch, X. Moreau, C. Thomassigny, and C. Greck Lett. Org. Chem. 6 2009 377 380
6. R. Ait-Youcef, K. Sbargoud, X. Moreau, and C. Greck Synlett 2009 3007 3010
7. R. Ait-Youcef, X. Moreau, and C. Greck J. Org. Chem. 75 2009 5312 5315
8. P.-M. Liu, C. Chang, R.-J. Reddy, Y.-F. Ting, H.-H. Kuan, and K. Chen Eur. J. Org. Chem. 2010 5705 5713
9. H. Vogt, S. Vanderheiden, and S. Bräse Chem. Commun. 2003 2448 2449
10. T. Baumann, H. Vogt, and S. Bräse Eur. J. Org. Chem. 2007 266 282
11. T. Baumann, M. Bächle, C. Hartmann, and S. Bräse Eur. J. Org. Chem. 2008 2207 2212
12. During the preparation of this manuscript, two publications have appeared: C. Liu, Q. Zhu, K.-W. Huang, and Y. Lu Org. Lett. 12 2011 2638 2641
13. J.-Y. Fu, Q.-C. Yang, Q.-L. Wang, J.-N. Ming, F.-Y. Wang, X.-Y. Xu, and L.-X. Wang J. Org. Chem. 76 2011 4661 4664
14. N.S. Chowdari, and C.F. Barbas III Org. Lett. 7 2005 867 870
15. J.T. Suri, D.D. Steiner, and C.F. Barbas III Org. Lett. 7 2005 3885 3888
16. J.-Y. Fu, X.-Y. Xu, Y.-C. Li, Q.-C. Huang, and L.-X. Wang Org. Biomol. Chem. 8 2010 4524 4526
17. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, and P. Melchiorre Angew. Chem., Int. Ed. 48 2009 7892 7894
18. A. Desmarchelier, J. Marrot, X. Moreau, and C. Greck Org. Biomol. Chem. 9 2011 994 997
19. 2O) to yield the desired product. The reaction has been scaled up 10-fold for the synthesis of (S)-ethyl phenylglycine methyl ester 8 without changes in the procedure.
20. For recent general reviews dealing with syntheses of α,α- dialkyl-α-aminoacids, see: V.A. Soloshonok, and A.E. Sorochinsky Synthesis 2010 2319 2344
21. C. Cativiela, and M.D. Diaz-de-Villegas Tetrahedron: Asymmetry 18 2007 569 623
22. H. Vogt, and S. Bräse Org. Biomol. Chem. 5 2007 406 430
23. J.A. Garbarino, J. Sierra, and R. Tapia J. Chem. Soc., Perkin Trans. 1 1973 1866 1869