Stereocontrol of all-carbon quaternary centers through enantioselective desymmetrization of meso primary diols by organocatalyzed acyl transfer

Angewandte Chemie - International Edition

Volumn 53, Issue 3, 2014, Pages 766-770

  Roux, Christèle ^a   Candy, Mathieu ^a   Pons, Jean Marc ^a   Chuzel, Olivier ^a   Bressy, Cyril ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

desymmetrization; meso compounds; organocatalysis; quaternary centers; tetrahydropyranes

Indexed keywords

CARBON; CATALYSTS; KETONES;

DESYM-METRIZATION; MESO COMPOUNDS; ORGANOCATALYSIS; QUATERNARY CENTERS; TETRAHYDROPYRANES;

ENANTIOSELECTIVITY;

EID: 84891886048     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308268     Document Type: Article

References (51)

1. A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745
2. J. Prakash Das, I. Marek, Chem. Commun. 2011, 47, 4593
3. C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295
4. M. Bella, T. Gasperi, Synthesis 2009, 1583.
5. Confusion between meso compounds and prochiral molecules exists and is persistent in current literature. In the "Basic Terminology of Stereochemistry", IUPAC defines a meso compound as "the achiral member(s) of a set of diastereomers which also includes one or more chiral members" (, G. P. Moss, Pure Appl. Chem. 1996, 68, 2193). This definition is not applicable to prochiral compounds such as the 2-methylpropane-1,3-diol, for example.
6. T. Honda, T. Koizumi, Y. Komatsuzaki, R. Yamashita, K. Kanai, H. Nagase, Tetrahedron: Asymmetry 1999, 10, 2703
7. S. Akai, T. Tsujino, E. Akiyama, K. Tanimoto, T. Naka, Y. Kita, J. Org. Chem. 2004, 69, 2478
8. V. Iosub, A. R. Haerl, J. Leung, M. Tang, K. Vembaiyan, M. Parvez, T. G. Back, J. Org. Chem. 2010, 75, 1612.
9. E. S. Sattely, S. J. Meek, S. J. Malcolmson, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 943
10. D. H. T. Phan, K. G. M. Kou, V. M. Dong, J. Am. Chem. Soc. 2010, 132, 16354
11. A. K. Mourad, J. Leutzow, C. Czekelius, Angew. Chem. 2012, 124, 11311
12. Angew. Chem. Int. Ed. 2012, 51, 11149.
13. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615
14. C. A. Leverett, V. C. Purohit, D. Romo, Angew. Chem. 2010, 122, 9669
15. Angew. Chem. Int. Ed. 2010, 49, 9479
16. F. Liu, X. Bugaut, M. Schedler, R. Fröhlich, F. Glorius, Angew. Chem. 2011, 123, 12834
17. Angew. Chem. Int. Ed. 2011, 50, 12626
18. M. Wilking, C. Mück-Lichtenfeld, C. G. Daniliuc, U. Hennecke, J. Am. Chem. Soc. 2013, 135, 8133.
19. M. H. Wu, K. B. Hansen, E. N. Jacobsen, Angew. Chem. 1999, 111, 2167
20. Angew. Chem. Int. Ed. 1999, 38, 2012
21. A. C. Spivey, S. J. Woodhead, M. Weston, B. I. Andrews, Angew. Chem. 2001, 113, 791
22. Angew. Chem. Int. Ed. 2001, 40, 769.
23. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2011, 111, PR 110.
24. Recent applications in total synthesis by our group: for Crocacin C, see:, M. Candy, G. Audran, H. Bienaymé, C. Bressy, J.-M. Pons, J. Org. Chem. 2010, 75, 1354; for a synthetic approach to Callystatin A, see
25. M. Candy, L. Tomas, S. Parat, V. Heran, H. Bienaymé, J.-M. Pons, C. Bressy, Chem. Eur. J. 2012, 18, 14267.
26. M. Candy, G. Audran, H. Bienaymé, C. Bressy, J.-M. Pons, Org. Lett. 2009, 11, 4950.
27. J. Y. Lee, Y. S. You, S. H. Kang, J. Am. Chem. Soc. 2011, 133, 1772.
28. D. Terakado, T. Oriyama, Org. Synth. 2006, 83, 70.
29. C. E. Müller, P. R. Schreiner, Angew. Chem. 2011, 123, 6136
30. Angew. Chem. Int. Ed. 2011, 50, 6012
31. A. Enríquez-García, E. P. Kündig, Chem. Soc. Rev. 2012, 41, 7803
32. M. D. Díaz-de-Villegas, J. A. Galvez, R. Badorrey, M. P. Lopez-Ram-de-Viu, Chem. Eur. J. 2012, 18, 13920.
33. T. Oriyama, K. Imai, T. Hosoya, T. Sano, Tetrahedron Lett. 1998, 39, 397
34. E. Vedejs, O. Daugulis, N. Tuttle, J. Org. Chem. 2004, 69, 1389
35. V. B. Birman, H. Jiang, X. Li, Org. Lett. 2007, 9, 3237
36. P. E. Kündig, A. Enriquez Garcia, T. Lomberget, P. Perez Garcia, P. Romanens, Chem. Commun. 2008, 3519.
37. R. P. Wurz, Chem. Rev. 2007, 107, 5570.
38. A. C. Spivey, S. Arseniyadis, Angew. Chem. 2004, 116, 5552
39. Angew. Chem. Int. Ed. 2004, 43, 5436
40. A. C. Spivey, S. Arseniyadis, Top. Curr. Chem. 2010, 291, 233
41. N. De Tycke, F. Couty, O. R. P. David, Chem. Eur. J. 2011, 17, 12852.
42. G. C. Fu, Acc. Chem. Res. 2000, 33, 412
43. G. C. Fu, Acc. Chem. Res. 2004, 37, 542
44. S. Yunmi Lee, J. M. Murphy, A. Ukai, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 15149, and references therein.
45. J. C. Ruble, J. Tweddell, G. C. Fu, J. Org. Chem. 1998, 63, 2794.
46. S. L. Schreiber, M. T. Goulet, G. Schulte, J. Am. Chem. Soc. 1987, 109, 4718.
47. A. Lattanzi, C. De Fusco, A. Russo, A. Poater, L. Cavallo, Chem. Commun. 2012, 48, 1650.
48. CCDC 942839 contains the supplementary crystallographic data available at the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
49. Y. Minko, M. Pasco, L. Lercher, M. Botoshansky, I. Marek, Nature 2012, 490, 522
50. P.-O. Delaye, D. Didier, I. Marek, Angew. Chem. 2013, 125, 5441
51. Angew. Chem. Int. Ed. 2013, 52, 5333.