Pd0/SnII promoted Barbier-type allylation and crotylation of sulfonimines

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7177-7180

  Roy, Ujjal Kanti ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; IMINE; PALLADIUM; PALLADIUM COMPLEX; SULFONAMIDE; SULFONE DERIVATIVE; TIN; TIN CHLORIDE;

ALLYLATION; ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; ROOM TEMPERATURE;

EID: 34548433000     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.201     Document Type: Article

References (57)

1. Reviews:. Li C.-J. Chem. Rev. 105 (2005) 3095-3165
2. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793
3. Marshall J.A. Chem. Rev. 100 (2000) 3163-3185
4. Thoonen S., Deelman B.J., and Koten G.V. Tetrahedron 59 (2003) 10261-10268
5. Takahara J.P., Masuyama Y., and Kurusu Y. J. Am. Chem. Soc. 114 (1992) 2577-2586
6. Selected references:. Tan X.-H., Shen B., Deng W., Zhao H., Liu L., and Guo Q.-X. Org. Lett. 5 (2003) 1833-1835
7. Tan X.-H., Shen B., Liu L., and Guo Q.-X. Tetrahedron Lett. 43 (2002) 9373-9376
8. Imai T., and Nishida S. J. Chem. Soc., Chem. Commun. (1994) 277-278
9. Masuyama Y., Takahara J.P., and Kurusu Y. Tetrahedron Lett. 30 (1989) 3437-3440
10. Masuyama Y., Takahara J.P., and Kurusu Y. J. Am. Chem. Soc. 110 (1988) 4473-4474
11. Roy U.K., and Roy S. Tetrahedron 62 (2006) 678-683
12. Banerjee M., Roy U.K., Sinha P., and Roy S. J. Organomet. Chem. 690 (2005) 1422-1428
13. Banerjee M., and Roy S. Org. Lett. 6 (2004) 2137-2140
14. Sinha P., and Roy S. Organometallics 23 (2004) 67-71
15. Banerjee M., and Roy S. Chem. Commun. (2003) 534-535
16. Kundu A., Prabhakar S., Vairamani M., and Roy S. Organometallics 18 (1999) 2782-2785
17. Kundu A., Prabhakar S., Vairamani M., and Roy S. Organometallics 16 (1997) 4796-4799
18. Felpin F.-X., Girard S., Vo-Thanh G., Robins R.J., Villieras J., and Lebreton J. J. Org. Chem. 66 (2001) 6305-6312
19. Wright D.L., Schulte II J.P., and Page M.A. Org. Lett. 2 (2000) 1847-1850
20. Laschat S., and Kunz H. J. Org. Chem. 56 (1991) 5883-5889
21. Reviews:. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895-1946
22. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
23. Selected recent references on imine allylation under non-Barbier conditions: allyl-Mg/Zn:. Jain R.P., and Williams R.M. J. Org. Chem. 67 (2002) 6361-6365
24. Sluis M.V.D., Dalmolen J., Lange B.D., Kaptein B., Kellogg R.M., and Broxterman Q.B. Org. Lett. 3 (2001) 3943-3946
25. Jones P., and Knochel P. J. Org. Chem. 64 (1999) 186-195
26. El-Shehawy A.A., Omara M.A., Ito K., and Itsuno S. Synlett (1998) 367-368
27. allyl-B:. Wada R., Shibuguchi T., Makino S., Oisaki K., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 7687-7691
28. Solin N., Wallner O.A., and Szabo K.J. Org. Lett. 7 (2005) 689-691
29. Itsuno S., Yokoi A., and Kuroda S. Synlett (1999) 1987-1989
30. allyl-Si:. Rabbat P.M.A., Valdez S.C., and Leighton J.L. Org. Lett. 8 (2006) 6119-6121
31. Friestad G.K., Korapala C.S., and Ding H. J. Org. Chem. 71 (2006) 281-289
32. Shimizu M., Itou H., and Miura M. J. Am. Chem. Soc. 127 (2005) 3296-3297
33. Yamasaki S., Fujii K., Wada R., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 124 (2002) 6536-6537
34. Billet M., Klotz P., and Mann A. Tetrahedron Lett. 42 (2001) 631-634
35. Wang D.-K., Zhou Y.-G., Tang Y., Hou X.-L., and Dai L.-X. J. Org. Chem. 64 (1999) 4233-4237
36. Nakamura K., Nakamura H., and Yamamoto Y. J. Org. Chem. 64 (1999) 2614-2615
37. allyl-Sn:. Colombo F., Annunziata R., and Benaglia M. Tetrahedron Lett. 48 (2007) 2687-2690
38. Li G.-I., and Zhao G. Synthesis (2006) 3189-3194
39. Wallner O.A., Olsson V.J., Eriksson L., and Szabo K.J. Inorg. Chim. Acta 359 (2006) 1767-1772
40. Szabo K.J. Synlett (2006) 811-824
41. Das B., Laxminarayana K., Ravikanth B., and Ramarao B. Tetrahedron Lett. 47 (2006) 9103-9106
42. Yin Y., Zhao G., and Li G.-L. Tetrahedron 61 (2005) 12042-12052
43. Fernandes R.A., Stimac A., and Yamamoto Y. J. Am. Chem. Soc. 125 (2003) 14133-14139
44. Aspinall H.C., Bissett J.S., Greeves N., and Levin D. Tetrahedron Lett. 43 (2002) 323-325
45. Fang X., Johannsen M., Yao S., Gathergood N., Hazell R.G., and Jorgensen K.A. J. Org. Chem. 64 (1999) 4844-4849
46. Nakamura H., Nakamura K., and Yamamoto Y. J. Am. Chem. Soc. 120 (1998) 4242-4243
47. For imine allylation under Barbier conditions, see:. Law M.C., Cheung T.W., Wong K.-Y., and Chan T.H. J. Org. Chem. 72 (2007) 923-929
48. Sun X.-W., Xu M.-H., and Lin G.-Q. Org. Lett. 8 (2006) 4979-4982
49. Vilaivan T., Winotapan C., Banphavichit V., Shinada T., and Ohfune Y. J. Org. Chem. 70 (2005) 3464-3471
50. Andrews P.C., Peatt A.C., and Raston C.L. Tetrahedron Lett. 45 (2004) 243-248
51. Yanada R., Negoro N., Okaniwa M., and Ibuka T. Tetrahedron 55 (1999) 13947-13956
52. Negoro N., Yanada R., Okaniwa M., Yanada K., and Fujita T. Synlett (1998) 835-836
53. Wang D.-K., Dai L.-X., Hou X.-L., and Zhang Y. Tetrahedron Lett. 37 (1996) 4187-4188
54. Estevam I.H.S., and Bieber L.W. Tetrahedron Lett. 44 (2003) 667-670
55. For chelation assisted allylation of N-tert-butylsulfinyl aldimines, see:. Foubelo F., and Yus M. Tetrahedron: Asymmetry 15 (2004) 3823-3825
56. Cogan D.A., Liu G., and Ellman J. Tetrahedron 55 (1999) 8883-8904
57. + = 354.1140; found, 354.1144.