Readily available (S)-proline-derived organocatalysts for the Lewis acid-mediated Lewis base-catalyzed stereoselective aldol reactions of activated thioesters

Tetrahedron

Volumn 68, Issue 39, 2012, Pages 8251-8255

  Bonsignore, Martina ^a   Benaglia, Maurizio ^a   Cozzi, Franco ^a   Genoni, Andrea ^a   Rossi, Sergio ^a   Raimondi, Laura ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Lewis base; Organocatalysis; Phosphoroamide; Tetrachlorosilane; Thioesters

Indexed keywords

ALDEHYDE; LEWIS ACID; LEWIS BASE; PROLINE; TERTIARY AMINE; THIOESTER;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84865064701     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.07.062     Document Type: Article

References (25)

1. T. Okhuma, and R. Noyori E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis: Supplement 1 2004 Springer New York, NY
2. C.A. Busacca, D.R. Fandrick, J.J. Song, and C.H. Senanayakea Adv. Synth. Catal. 353 2011 1825
3. P.T. Anastas Green Chemistry Textbook 2004 Oxford University Press New York, NY
4. A. Berkessel, H. Groger, Asymmetric Organic Catalysis 2005 Wiley-VCH Weinheim
5. For a review on Lewis base-catalyzed reactions see: S.E. Denmark, and G.L. Beutner Angew. Chem., Int. Ed. 47 2008 1560
6. S. Rossi, M. Benaglia, A. Genoni, T. Benincori, and G. Celentano Tetrahedron 67 2011 158
7. S.E. Denmark, T. Wynn, and G.L. Beutner J. Am. Chem. Soc. 124 2002 13405
8. S.E. Denmark, and R.A. Stavenger Acc. Chem. Res. 33 2000 432
9. S.E. Denmark, B.M. Eklov, P.J. Yao, and M.D.J. Eastgate J. Am. Chem. Soc. 131 2009 11170 and references cited
10. A. Massa, A. Roscigno, P. De Caprariis, R. Filosa, and A. Di Mola Adv. Synth. Catal. 352 2010 3348 and references cited
11. M. Benaglia, S. Guizzetti, and L. Pignataro Coord. Chem. Rev. 252 2008 492
12. M. Benaglia, S. Guizzetti, and S. Rossi Silicate-mediated Stereoselective Reactions Catalyzed by Chiral Lewis bases M. Gruttadauria, F. Giacalone, Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques and Applications 2011 John Wiley and Sons Hoboken, NJ
13. S. Kotani, S. Hashimoto, and M. Nakajima Tetrahedron 63 2007 3122
14. M. Sugiura, N. Sato, S. Kotani, and M. Nakajima Chem. Commun. 2008 4309
15. M. Sugiura, M. Kumahara, and M. Nakajima Chem. Commun. 2009 3585
16. S. Kotani, Y. Shimoda, M. Sugiura, and M. Nakajima Tetrahedron Lett. 50 2009 4602
17. M. Sugiura, N. Sato, Y. Sonoda, S. Kotani, and M. Nakajima Chem. Asian J. 5 2010 478
18. For a recent review article dedicated to the use of chiral phosphine oxides in organocatalysis see: S. Rossi, and M. Benaglia Org. Biomol. Chem. 8 2010 3824
19. V. Simonini, M. Benaglia, and T. Benincori Adv. Synth. Catal. 350 2008 561
20. S. Rossi, M. Benaglia, F. Cozzi, A. Genoni, and T. Benincori Adv. Synth. Catal. 353 2011 848
21. Compounds 3 and 4 had been previously synthesized and tested in the Lewis-base catalyzed stereoselective reduction of ketoimines with trichlorosilane (for a review see: S. Guizzetti, and M. Benaglia Eur. J. Org. Chem. 2010 5529 ) showing to be particularly efficient in the reduction of β-iminoesters to β-aminoesters that was performed in high yields and up to 85% enantioselectivity:
22. M. Bonsignore, M. Benaglia, R. Annunziata, and G. Celentano Synlett 2011 1085
23. In ancillary experiments it was found that catalysts 3 and 4 promoted the direct aldol reaction between cyclohexanone and benzaldehyde (DCM, 0 °C, 24 h) in 25% yield, 76:24 anti/syn, 25% ee for anti isomer and 65% yield, 70:30 anti/syn, 12% ee for anti isomer, respectively. For a recent contribution in the field see: S. Kotani, S. Aoki, M. Sugiura, and M. Nakajima Tetrahedron Lett. 52 2011 2834
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.02 2009 Gaussian Wallingford CT
25. MacroModel, Version 9.9 2011 Schrödinger New York, NY