Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

Tetrahedron Asymmetry

Volumn 21, Issue 5, 2010, Pages 601-616

  Duguet, Nicolas ^a   Donaldson, Adele ^a   Leckie, Stuart M ^a   Kallström, Eddy A ^a   Campbell, Craig D ^a   Shapland, Peter ^b   Brown, Thomas B ^c   Slawin, Alexandra M Z ^a   Smith, Andrew D ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; CARBENOID; IMIDAZOLINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 77953136499     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.002     Document Type: Article

References (53)

1. For an excellent recent review of Lewis-base mediated reaction processes see:. Denmark S.E., and Beutner G.L. Angew. Chem., Int. Ed. 47 (2008) 1560-1638
2. Thomson J.E., Rix K., and Smith A.D. Org. Lett. 8 (2006) 3785-3788
3. Thomson J.E., Campbell C.D., Concellón C., Duguet N., Rix K., Slawin A.M.Z., and Smith A.D. J. Org. Chem. 73 (2008) 2784-2791
4. Campbell C.D., Duguet N., Gallagher K.A., Thomson J.E., Lindsay A.G., O'Donoghue A., and Smith A.D. Chem. Commun. (2008) 3528-3530
5. Joannesse C., Simal C., Concellón C., Thomson J.E., Campbell C.D., Slawin A.M.Z., and Smith A.D. Org. Biomol. Chem. 6 (2008) 2900-2907
6. Thomson J.E., Kyle A.F., Concellón C., Gallagher K.A., Lenden P., Morrill L.C., Miller A.J., Joannesse C., Slawin A.M.Z., and Smith A.D. Synthesis 17 (2008) 2805-2818
7. Joannesse C., Johnston C.P., Concellón C., Simal C., Philp D., and Smith A.D. Angew. Chem., Int. Ed. 48 (2009) 8914-8918
8. Concellón C., Duguet N., and Smith A.D. Adv. Synth. Catal. 351 (2009) 3001-3009
9. For recent reviews of the ability of NHCs to catalyse organocatalytic processes see:. Enders D., Niemeier O., and Henseler A. Chem. Rev. 107 (2007) 5606-5655
10. Marion N., Díez-González S., and Nolan S.P. Angew. Chem., Int. Ed. 46 (2007) 2988-3000
11. For elegant studies by the Ye group utilising NHCs in asymmetric catalysis using ketenes see:. Zhang Y.R., He L., Wu X., Shao P.L., and Ye S. Org. Lett. 10 (2008) 277-280
12. Zhang Y.-R., Lv H., Zhou D., and Ye S. Chem. Eur. J. 14 (2008) 8473-8476
13. Huang X.-L., He L., Shao L.P.-L., and Ye S. Angew. Chem., Int. Ed. 48 (2009) 192-195
14. Lv H., Zhang Y.-R., Huang X.-L., and Ye S. Adv. Synth. Catal. 350 (2008) 2715-2718
15. He L., Lv H., Zhang Y.-R., and Ye S. J. Org. Chem. 73 (2008) 8101-8103
16. For our preliminary studies concerning the asymmetric synthesis of β-lactams using NHCs see:. Duguet N., Campbell C.D., Slawin A.M.Z., and Smith A.D. Org. Biomol. Chem. 6 (2008) 1108-1113
17. Duguet N., Donaldson A., Leckie S.M., Douglas J., Shapland P., Churchill G., Slawin A.M.Z., and Smith A.D. Tetrahedron: Asymmetry 21 (2010) 582-600
18. For reviews of stereochemical relay and it applications see:. Corminboeuf O., Quaranta L., Renaud P., Liu M., Jasperse C.P., and Sibi M.P. Chem. Eur. J. 9 (2003) 28-35
19. Walsh P.J., Lurain A.E., and Balsells J. Chem. Rev. 103 (2003) 3297-3344
20. Clayden J., and Vassiliou N. Org. Biomol. Chem. 4 (2006) 2667-2678
21. Mikami K., and Yamanaka M. Chem. Rev. 103 (2003) 3369-3400
22. For select manuscripts that use this concept see:. Bull S.D., Davies S.G., Epstein S.W., Leech M.A., and Ouzman J.V.A. J. Chem. Soc., Perkin Trans. 1 (1998) 2321-2330
23. Bull S.D., Davies S.G., Fox D.J., and Sellers T.G.R. Tetrahedron: Asymmetry 9 (1998) 1483-1487
24. Bull S.D., Davies S.G., Epstein S.W., and Ouzman J.V.A. Chem. Commun. (1998) 659-660
25. Bull S.D., Davies S.G., Fox D.J., Garner A.C., and Sellers T.G.R. Pure Appl. Chem. 70 (1998) 1501-1506
26. Watanabe Y., Mase N., Furue R., and Toru T. Tetrahedron Lett. 42 (2001) 2981-2984
27. Davis T.J., Balsells J., Carroll P.J., and Walsh P.J. Org. Lett. 3 (2001) 2161-2164
28. Balsells J., and Walsh P.J. J. Am. Chem. Soc. 122 (2000) 1802-1803
29. Evans D.A., Campos K.R., Tedrow J.S., Michael F.E., and Gagne M.R. J. Am. Chem. Soc. 122 (2000) 7905-7920
30. Hiroi K., and Ishii M. Tetrahedron Lett. 41 (2000) 7071-7074
31. Wada E., Pei W., and Kanemasa S. Chem. Lett. (1994) 2345-2348
32. Wada E., Yasuoka H., and Kanemasa S. Chem. Lett. (1994) 1637-1640
33. Malkov A.V., Stoncius S., MacDougall K.N., Mariani A., McGeoch G.D., and Kocovsky P. Tetrahedron 62 (2005) 264-284
34. Malkov A.V., Hand J.B., and Kocovsky P. Chem. Commun. (2003) 1948-1949
35. Maughan M.A.T., Davies I.G., Claridge T.D.W., Courtney S., Hay P., and Davis B.G. Angew. Chem., Int. Ed. 42 (2003) 3788-3792
36. Belokon Y.N., Fuentes J., North M., and Steed J.W. Tetrahedron 60 (2004) 3191-3204
37. Tye H., Eldred C., and Wills M. Tetrahedron Lett. 43 (2002) 155-158
38. Pytkowicz J., Roland S., and Mangeney P. J. Organomet. Chem. 631 (2001) 157-163
39. Hilgraf R., and Pfaltz A. Adv. Synth. Catal. 347 (2005) 61-77
40. Roland S., Mangeney P., and Alexakis A. Synthesis 2 (1999) 228-230
41. Grasa G.A., Singh R., Scott N.M., Stevens E.D., and Nolan S.P. Chem. Commun. (2004) 2890-2891
42. Schmidt M.A., Müller P., and Movassaghi M. Tetrahedron Lett. 49 (2008) 4316-4318
43. Alvaro G., Grepioni F., and Savoia D. J. Org. Chem. 62 (1997) 4180-4182
44. Bambridge K., Begley M.J., and Simpkins N.S. Tetrahedron Lett. 35 (1994) 3391-3394
45. Rodeschini V., Simpkins N.S., and Zhang F. Org. Synth. 84 (2007) 306
46. 2).
47. Alexakis A., Aujard I., Kanger T., and Mangeney P. Org. Synth. Coll. Vol. 10 (2004) 312
48. Guillen F., Winn C.L., and Alexakis A. Tetrahedron: Asymmetry 15 (2001) 2083-2086
49. Kobayashi S., Matsubara R., Nakamura Y., Kitagawa H., and Sugiura M. J. Am. Chem. Soc. 125 (2003) 2507-2515
50. Winn C.L., Guillen F., Pytkowicz J., Roland S., Mangeney P., and Alexakis A. J. Organomet. Chem. 690 (2005) 5672-5695
51. Fujita Y., Tsuda Y., Li T., Motoyama T., Takahashi M., Shimizu Y., Yokoi T., Sasaki Y., Ambo A., Kita A., Jinsmaa Y., Bryant S.D., Lazarus L.H., and Okada Y. J. Med. Chem. 47 (2004) 3591-3599
52. Adrián F., Burguete M.I., Fraile J.M., García J.I., García J., García-España E., Luis S.V., Mayoral J.A., Royo A.J., and Sanchez M.C. Eur. J. Inorg. Chem. 12 (1999) 2347-2354
53. Ishara K., and Nakano K. J. Am. Chem. Soc. 127 (2005) 10504-10505