Unexpected highly diastereoconvergent Grignard additions to d-xylofuranose-derived t-butanesulfinyl aldimines

Tetrahedron Letters

Volumn 53, Issue 2, 2012, Pages 119-122

  Wang, Bing ^a   Zhang, Pei Pei ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Addition; Carbohydrate; Diastereoconvergent; Grignard reagent; t Butanesulfinyl imine

Indexed keywords

5,5' DITHIOBIS(2 NITROBENZOIC ACID); BUTANESULFINYLALDIMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; IMINE; ORGANOMETALLIC COMPOUND; SOLVENT; SULFINIMINE; UNCLASSIFIED DRUG; XYLOFURANOSE; XYLOSE;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; DIASTEREOCONVERGENCE; GRIGNARD REACTION; STEREOCHEMISTRY;

EID: 83555178390     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.002     Document Type: Article

References (38)

1. For leading reviews, see: M.T. Robak, M.A. Herbage, and J.A. Ellman Chem. Rev. 110 2010 3600
2. F. Ferreira, C. Botuha, F. Chemla, and A. Pérez-Luna Chem. Soc. Rev. 38 2009 1162
3. G.-Q. Lin, M.-H. Xu, Y.-W. Zhong, and X.-W. Sun Acc. Chem. Res. 41 2008 831
4. For examples of predominant stereo-induction of chiral t-BS over that of α-substituents, see: A. Voituriez, A. Pérez-Luna, F. Ferreira, C. Botuha, and F. Chemla Org. Lett. 11 2009 931
5. T. Hjelmgaard, S. Faure, P. Lemoine, B. Viossat, and D.J. Aitken Org. Lett. 10 2008 841
6. J.W. Evans, and J.A. Ellman J. Org. Chem. 68 2003 9948
7. J. Liu, Y. Li, and J. Hu J. Org. Chem. 72 2007 3119
8. G.K.S. Prakash, M. Mandal, and G.A. Olah J. Am. Chem. Soc. 124 2002 6538
9. J.P. McMahon, and J.A. Ellman Org. Lett. 6 2004 1645
10. M.D.P. Risseeuw, J. Mazurek, A. van Langenvelde, G.A. van der Marel, H.S. Overkleeft, and M. Overhand Org. Biomol. Chem. 5 2007 2311
11. B. Wang J. Org. Chem. 75 2010 6012 This is not to be confused with reversal of stereoselectivity, which is relatively common for this chiral auxiliary upon variation of reaction conditions (solvent, countercation, additive)
12. B.-L. Chen, B. Wang, and G.-Q. Lin J. Org. Chem. 75 2010 941
13. B. Wang, and G.-Q. Lin Eur. J. Org. Chem. 2009 5038
14. B. Wang, and Y.-J. Wang Org. Lett. 11 2009 3410
15. B. Wang, Z. Zhong, and G.-Q. Lin Org. Lett. 11 2009 2011
16. B. Wang, and R.-H. Liu Eur. J. Org. Chem. 2009 2845
17. R.-H. Liu, K. Fang, B. Wang, M.-H. Xu, and G.-Q. Lin J. Org. Chem. 73 2008 3307
18. B. Wang, K. Fang, and G.-Q. Lin Tetrahedron Lett. 44 2003 7981
19. B. Wang, X.-M. Yu, and G.-Q. Lin Synlett 2001 904
20. D.-G. Liu, B. Wang, and G.-Q. Lin J. Org. Chem. 65 2000 9114
21. Z.-H. Sun, and B. Wang J. Org. Chem. 73 2008 2462
22. For leading references, see: E. Racine, C. Bello, S. Gerber-Lemaire, P. Vogel, and S. Py J. Org. Chem. 74 2009 1766
23. N.S. Karanjule, S.D. Markad, V.S. Shinde, and D.D. Dhavale J. Org. Chem. 71 2006 4667
24. N.S. Karanjule, S.D. Markad, and D.D. Dhavale J. Org. Chem. 71 2006 6273
25. G. Masson, C. Philouze, and S. Py Org. Biomol. Chem. 3 2005 2067
26. For pyranose-derived sulfinimines, see: M. Raunkjær, F.E. Oualid, G.A. van der Marel, H.S. Overkleeft, and M. Overhand Org. Lett. 6 2004 3167
27. For a ribose-derived t-BS imine, see: Y.-C. Luo, H.-H. Zhang, and P.-F. Xu Synlett 2009 833 No anomalous result was reported
28. D.G. Drueckhammer, and C.-H. Wong J. Org. Chem. 50 1985 5912
29. G.W.J. Fleet, and P.W. Smith Tetrahedron 43 1987 971
30. K. Nacro, J. Lee, J.J. Barchi, N.E. Lewin, P.M. Blumberg, and V.E. Marquez Tetrahedron 58 2002 5335
31. G. Liu, D.A. Cogan, T.D. Owens, T.P. Tang, and J.A. Ellman J. Org. Chem. 64 1999 1278
32. CCDC 720014 contains the crystallographic data for 3a. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
33. CCDC 730904 contains the crystallographic data for 3d. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
34. G. Liu, D.A. Cogan, and J.A. Ellman J. Am. Chem. Soc. 119 1997 9913
35. D.A. Cogan, G. Liu, and J.A. Ellman Tetrahedron 55 1999 8883 THF was found to be deleterious to dr in the latter paper
36. D.J. Hart, W.P. Hong, and L.Y. Hsu J. Org. Chem. 52 1987 4665
37. For selected papers, see: P. Compain, O.R. Martin, C. Boucheron, G. Godin, L. Yu, K. Ikeda, and N. Asano ChemBioChem 7 2006 1356
38. A. Bordier, P. Compain, O.R. Martin, K. Ikeda, and N. Asano Tetrahedron: Asymmetry 14 2003 47 The carbohydrate moiety reported (l-xylo-) was antipodal with that of 2 in our work, however, the relative sense of chiral induction was the same