A novel and efficient synthesis of chiral C2-symmetric 1,4-diamines

Tetrahedron Letters

Volumn 50, Issue 5, 2009, Pages 552-554

  Xu, Lianhong ^a   Desai, Manoj C ^a   Liu, Hongtao ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

C2 symmetric 1,4 diamines; Corey Winter olefination

Indexed keywords

CARBON; DIAMINE DERIVATIVE;

ARTICLE; OLEFINATION; PINACOL REARRANGEMENT; SYNTHESIS;

EID: 57549119096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.071     Document Type: Article

References (21)

1. Fache F., Schulz E., Tommasino M.L., and Lemaire M. Chem. Rev. 100 (2000) 2159 and references cited therein
2. Lucet D., Le Gall T., and Mioskowski C. Angew. Chem., Int. Ed. 37 (1998) 2580-2627 and references cited therein
3. Kempf D.J., Sham H.L., Marsh K.C., Flentge C.A., Betebenner D., Green B.E., McDonald E., Vasavanonda S., Saldivar A., Wideburg N.E., Kati W.M., Ruiz L., Zhao C., Fino L., Patterson J., Molla A., Plattner J.J., and Norbeck D.W. J. Med. Chem. 41 (1998) 602
4. Barton D.H.R., and McCombie S.W. J. Chem. Soc., Perkin Trans. 1 (1975) 1574
5. Hodgson D.M., Humphreys P.G., Miles S.M., Brieley C.A., and Ward J.G. J. Org. Chem. 72 (2007) 10009
6. Hodgson D.M., and Miles S.M. Angew. Chem., Int. Ed. 45 (2006) 935
7. Enders D., and Meiers M. Synthesis 17 (2003) 2542
8. Yamauchi T., Higashiyama K., Kubo H., and Ohmiya S. Tetrahedron: Asymmetry 11 (2000) 30003
9. Gurjar M.K., Pal S., Rao A.V.R., Pariza R.J., and Chorghade M.S. Tetrahedron 53 (1997) 4769
10. Rao A.V.R., Gurjar M.K., Pal S., Pariza R.J., and Chroghade M.S. Tetrahedron Lett. 36 (1995) 2505
11. Beier C., Schaumann E., and Adiwidjaja G. Synlett (1998) 41
12. Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58
13. Alcón M., Canas M., Poch M., Moyano A., Pericàs M.A., and Riera A. Tetrahedron Lett. 35 (1994) 1589
14. Alcón M., Poch M., Moyano A., and Pericàs M.A. Tetrahedron: Asymmetry 8 (1997) 2967
15. Robertson J., Stafford P.M., and Bell S.J. J. Org. Chem. 70 (2005) 7133
16. Mergmann M., and Zervas L. Ber. 65 (1932) 1192
17. Sergeev M.E., Pronin V.B., and Voyushina T.L. Synlett (2005) 2802
18. Debaene F., Silva J.A.D., Pianowski Z., Durran F.J., and Winssinger N. Tetrahedron 63 (2007) 6577
19. Nakamura M., Miyashita H., Yamaguchi M., Shirasaki Y., Nakamura Y., and Inoue J. Bioorg. Med. Chem. 11 (2003) 5449
20. Lam P.Y.S., Ru Y., Jadhav P.K., Aldrich P.E., DeLucca G.V., Eyermann C.J., Chang C., Emmett G., Holler E.R., Daneker W.F., Li L., Confalone P.N., McHugh R.J., Han Q., Li R., Markwalder J.A., Seitz S.P., Sharpe T.R., Bacheler L.T., Rayner M.M., Klabe R.M., Shum L., Winslow D.L., Kornhauser D.M., Jackson D.A., Erickson-Viitanen S., and Hodge C.N. J. Med. Chem. 39 (1996) 3514
21. 3) δ 7.4-7.0 (20H, m), 5.47 (2H, m), 5.07 (4H, s), 4.62 (2H, m), 4.45 (2H, m), 2.78 (4H, d, J = 6.1 Hz).