(N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: Preparation and application for the syntheses of 1,2-diols

Tetrahedron

Volumn 68, Issue 42, 2012, Pages 8704-8711

  Ma, Lu ^a,b   Zhao, Dongmei ^b   Chen, Lin ^a   Wang, Xin ^a   Chen, Yue Lei ^a   Shen, Jingkang ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

1,2 Diols; Aldehydes; N,N Diisopropylcarbamoyl; Nucleophilic addition; Regioselective protection

Indexed keywords

(N,N DIISOPROPYLCARBAMOYLOXY)METHYL 4 TOLYL SULFONE; 1 (N,N DIISOPROPYLCARBAMOYLOXY) 1 TOSYLMETHANE; CARBAMOYL PHOSPHATE; CARBONYL DERIVATIVE; GRIGNARD REAGENT; METAL; N,N DIISOPROPYLCARBAMOYL; PARAFORMALDEHYDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEPROTONATION; DRUG SYNTHESIS; GRIGNARD REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84865743913     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.08.025     Document Type: Article

References (37)

1. B.M. Trost, S. Malhotra, P. Koschker, and P. Ellerbrock J. Am. Chem. Soc. 134 2011 2075 2084
2. J. Seayad, A.M. Seayad, and C.L.L. Chai Org. Lett. 12 2010 1412 1415
3. C.P. Park, J.H. Lee, K.S. Yoo, and K.W. Jung Org. Lett. 12 2010 2450 2452
4. J.C. Griffith, K.M. Jones, S. Picon, M.J. Rawling, B.M. Kariuki, M. Campbell, and N.C.O. Tomkinson J. Am. Chem. Soc. 132 2010 14409 14411
5. B.C. Giglio, V.A. Schmidt, and E.J. Alexanian J. Am. Chem. Soc. 133 2011 13320 13322
6. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 2547
7. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 6th ed. 2007 John Wiley & Sons Hoboken, NJ
8. R.C. Larock Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd ed. 1999 John Wiley & Sons New York, NY pp 961-1196
9. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley & Sons New York, NY pp 17-245
10. G.M. Hodgson Organolithiums in Enantioselective Synthesis Topics in Organometallic Chemistry 2003 Springer Berlin/Heidelberg, Germany
11. D. Hoppe, and T. Hense Angew. Chem., Int. Ed. 36 1997 2282 2316
12. P. Beak, A. Basu, D.J. Gallagher, Y.S. Park, and S. Thayumanavan Acc. Chem. Res. 29 1996 552 560
13. D. Hoppe Synthesis 2009 43 55
14. R.P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H.K. Scott, and V.K. Aggarwal Angew. Chem., Int. Ed. 50 2011 3760 3763
15. S. Nave, R.P. Sonawane, T.G. Elford, and V.K. Aggarwal J. Am. Chem. Soc. 132 2010 17096 17098
16. J.L. Stymiest, V. Bagutski, R.M. French, and V.K. Aggarwal Nature 456 2008 778 782
17. M. Reggelin, P. Tebben, and D. Hoppe Tetrahedron Lett. 30 1989 2915 2918
18. P. Tebben, M. Reggelin, and D. Hoppe Tetrahedron Lett. 30 1989 2919 2922
19. D. Hoppe, P. Tebben, M. Reggelin, and M. Bolte Synthesis 1997 183 190
20. D. Hoppe, T. Kraemer, J.-R. Schwark, and O. Zschage Pure Appl. Chem. 62 1990 1999 2006
21. Y.-L. Chen, and D. Hoppe J. Org. Chem. 74 2009 4188 4194
22. Y.-L. Chen, and D. Hoppe Tetrahedron: Asymmetry 20 2009 1561 1567
23. F. Hintze, and D. Hoppe Synthesis 12 1992 1216 1218
24. M.J. Cravey, and H. Kohn J. Am. Chem. Soc. 102 1980 3928 3939
25. G. Boche, F. Bosold, J.C.W. Lohrenz, A. Opel, and P. Zulauf Chem. Ber. 126 1993 1873 1885
26. M. Özlügedik, J. Kristensen, B. Wibbeling, R. Fröhlich, and D. Hoppe Eur. J. Org. Chem. 2002 414 427
27. L.-L. Gundersen, and T. Benneche Acta Chem. Scand. 45 1991 975 977
28. Aside from accelerating the reaction between lithium metal and n-butyl halides, sodium impurity in lithium plays certain role in other reactions, too. See for example: H.M. Walborsky, and R.B. Banks Bull. Soc. Chim. Belg. 89 1980 849 868
29. The migration of OCb protection is unexpected since it is known to be quite stable under such conditions: see for example Y.L. Chen, R. Frohlich, and D. Hoppe Tetrahedron: Asymmetry 20 2009 1144 1149
30. L. Vares, and T. Rein J. Org. Chem. 67 2002 7226 7237
31. K. Kraehenbuehl, S. Picasso, and P. Vogel Helv. Chim. Acta 81 1998 1439 1479
32. J.B. Martin J. Am. Chem. Soc. 75 1953 5483 5486
33. Ma, L.; Chen, Y. -L., unpublished results in this lab.
34. D. Kapeller, R. Barth, K. Mereiter, and F. Hammerschmidt J. Am. Chem. Soc. 129 2007 914 923
35. B. Plietker, M. Niggemann, and A. Pollrich Org. Biomol. Chem. 2 2004 1116 1124
36. K.C. Nicolaou, S.A. Snyder, D.A. Longbottom, A.Z. Nalbandian, and X. Huang Chem. - Eur. J. 10 2004 5581 5606
37. J. Ortiz, A. Guijarro, and M. Yus Eur. J. Org. Chem. 1999 3005 3012