Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

Tetrahedron Asymmetry

Volumn 18, Issue 15, 2007, Pages 1833-1843

  Cheng, Liang ^a,b   Liu, Li ^a   Sui, Yong ^a,b   Wang, Dong ^a   Chen, Yong Jun ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

(2 INDOLYL)METHANAMINE DERIVATIVE; IMINE; INDOLE DERIVATIVE; LEWIS ACID; N PHENYLSULFONYLINDOLE DERIVATIVE; N TERT BUTANESULFINYL ALDIMINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; LITHIATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 34548404275     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.07.029     Document Type: Article

References (48)

1. Sundberg R.J. Indoles (1996), Academic Press, San Diego
2. Hegedus L.S. Angew. Chem., Int. Ed. Engl. 27 (1988) 1113-1126
3. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045-1075
4. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873-2920
5. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875-2911
6. Sundberg R.J. In: Blomquist A.T. (Ed). The Chemistry of Indoles (1970), Academic Press, New York
7. Modi S.P., Zayed A.-H., and Archer S. J. Chem. Soc., Chem. Commun. (1970) 1095-1096
8. Brown R.K. In: Houlihan W.J. (Ed). Heterocyclic Compounds Vol. 25 (1972), Wiley-Interscience, New York
9. Kuehne M.E., Podhorez D.E., Mulamba T., and Bornmann W.G. J. Org. Chem. 52 (1987) 347-353
10. Leon P., Garbay-Jaureguiberry C., Barsi M.C., Le pecq J.B., and Roques B.P. J. Med. Chem. 30 (1987) 2074-2080
11. Hashimoto C., and Husson H.-P. Tetrahedron Lett. 29 (1988) 4563-4566
12. Laronze M., and Sapi J. Tetrahedron Lett. 43 (2002) 7925-7928
13. For examples on the applications of 2-lithioindoles, see:. Hasan I., Marinelli E.R., Chang L.-C., Fowler F.W., and Levy A.B. J. Org. Chem. 46 (1981) 157-164
14. Gmeiner P., Kraxner J., and Bollinger B. Synthesis 10 (1996) 1196-1198
15. Manabe S., and Ito Y. J. Am. Chem. Soc. 121 (1999) 9754-9755
16. Kraxner J., and Gmeiner P. Synthesis 8 (2000) 1081-1083
17. For other 2-metallated indoles, see Palladium:. Itahara T., Ikeda M., and Sakakibara T. J. Chem. Soc., Perkin Trans. 1 (1983) 1361-1363
18. Magnesium:. Kondo Y., Yoshida A., and Sakamoto T. J. Chem. Soc., Perkin Trans. 1 (1996) 2331-2332
19. Stannium:. Beddoes R.L., Cheeseright T., Wang J., and Quayle P. Tetrahedron Lett. 36 (1995) 283-286
20. Jia Y.-X., Xie J.-H., Duan H.-F., Wang L.-X., and Zhou Q.-L. Org. Lett. 8 (2006) 1621-1624
21. Wang Y.-Q., Song J., Hong R., Li H., and Deng L. J. Am. Chem. Soc. 128 (2006) 8156-8157
22. Kang Q., Zhao Z.-A., and You S.-L. J. Am. Chem. Soc. 129 (2007) 1484-1485
23. Varney M.D., Appelt K., Kalish V., Reddy R., Tatlock J., Palmer C.L., Romines W.H., Wu B.-W., and Musick L. J. Med. Chem. 37 (1994) 2274-2284
24. Giorgioni G., Accorroni B., Stefano A.D., Marucci G., Siniscalchi A., and Claudi F. Med. Chem. Res. 14 (2005) 57-73
25. Cozzi P.G., Prati G.P., and Umani-Ronchi A. Gazz. Chim. Ital. 127 (1997) 403-405
26. Sundberg R.J., and Russell H.F. J. Org. Chem. 38 (1973) 3324-3330
27. Love B.E., and Raje P.S. J. Org. Chem. 59 (1994) 3219-3222
28. Enders D., and Signore G.D. Tetrahedron: Asymmetry 15 (2004) 747-751
29. Davis F.A., Zhou P., and Chen B. Chem. Soc. Rev. 1 (1998) 13-18
30. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984-995
31. Zhou P., Chen B., and Davis F.A. Tetrahedron 60 (2004) 8003-8030
32. Davis F.A., Yang B., Deng J., and Zhang J. ARKIVOC vii (2006) 120-128
33. Senanayaka C.H., Krishnamurthy D., Lu Z.-H., Han Z., and Gallou I. Aldrichim. Acta 38 (2005) 93-104
34. Morton D., and Stockman R.A. Tetrahedron 62 (2006) 8869-8905
35. Kochi T., Tang T.P., and Ellman J.A. J. Am. Chem. Soc. 125 (2003) 11276-11282
36. Kochi T., and Ellman J.A. J. Am. Chem. Soc. 126 (2004) 15652-15653
37. Davis F.A., and Yang B. J. Am. Chem. Soc. 127 (2005) 8398-8407
38. Beenen M.A., Deix D.J., and Ellman J.A. J. Am. Chem. Soc. 128 (2006) 6304-6305
39. Borg G., Chino M., and Ellman J.A. Tetrahedron Lett. 42 (2001) 1433-1435
40. Yamamoto Y., Komatsu T., and Maruyama K. J. Am. Chem. Soc. 106 (1984) 5031-5033
41. Yamamoto Y., Maruyama K., Komatsu T., and Ito W. J. Am. Chem. Soc. 108 (1986) 7778-7786
42. Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 121 (1999) 268-269
43. Cogan D.A., Liu G., and Ellman J.A. Tetrahedron 55 (1999) 8883-8904
44. Jiang W., Chen C., Marinkovic D., Tran J.A., Chen C.W., Arellano L.M., White N.S., and Tucci F.C. J. Org. Chem. 70 (2005) 8924-8931
45. Uchiyama M., Matsumoto Y., Nakamura S., Ohwada T., Kobayahsi N., Yamashita N., Matsumiya A., and Sakamoto T. J. Am. Chem. Soc. 126 (2004) 8755-8759
46. Bolshan Y., and Batey R.A. Org. Lett. 7 (2005) 1481-1484
47. Beenen M.A., Weix D.J., and Ellman J.A. J. Am. Chem. Soc. 128 (2006) 6304-6305
48. Jiang W., Chen C., Marinkovic D., Tran J.A., Chen C.W., Arellano L.M., White N.S., and Tucci F.C. J. Org. Chem. 70 (2005) 8924-8931