Asymmetric synthesis of (2S,3R)-(-)-epi-CP-99,994 using sulfinimine-derived anti-2,3-diamino esters

Tetrahedron Letters

Volumn 50, Issue 37, 2009, Pages 5205-5207

  Davis, Franklin A ^a   Zhang, Yanfeng ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 METHOXYBENZYLAMINO) 2 PHENYLPIPERIDINE; CARBENE; DIAMINE; DIBENZYLAMINE; ESTER; IMINE; PIPERIDINE DERIVATIVE; SULFUR DERIVATIVE;

ALLYLATION; AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEPROTECTION REACTION; DRUG HYDROLYSIS; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 67650876482     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.125     Document Type: Article

References (24)

1. For a review on the syntheses and significance of 2,3-diamino esters see:. Viso A., Pradilla R.F.d.l., Garcia A., and Flores A. Chem. Rev. 105 (2005) 3167-3198
2. For reviews highlighting the importance of vicinal diamines see:. Sababu Kotti S.R.S., Cody T., and Li G. Biol. Drug Des. 67 (2006) 101
3. Lucet D., Le Gall T., and Mioskowski C. Angew. Chem., Int. Ed 37 (1998) 2580
4. For recent reviews on the chemistry of sulfinimines see:. Zhou P., Chen B.-C., and Davis F.A. Tetrahedron 60 (2004) 8003-8030
5. Senanayake C.H., Krishnamurthy D., Lu Z.-H., Han Z., and Gallou I. Aldrichim. Acta 38 (2005) 93-104
6. Morton D., and Stockman R.A. Tetrahedron 62 (2006) 8869-8905
7. Davis F.A. J. Org. Chem. 71 (2006) 8993-9003
8. Davis F.A., and Deng J. Org. Lett. 6 (2004) 2789-2792
9. Davis F.A., Zhang Y., and Qiu H. Org. Lett. 9 (2007) 833-836
10. Davis F.A., and Deng J. Org. Lett. 7 (2005) 621-623
11. Davis F.A., Zhang J., Zhang Y., and Qiu H. Synth. Commun. 39 (2009) 1914-1919
12. Davis F.A., Zhang Y., and Li D. Tetrahedron Lett. 48 (2007) 7838-7840
13. For other examples of the asymmetric synthesis of heterocycles using sulfinimine-derived 2,3-diamino esters see:. Viso A., Fernandez de la Pradilla R., and Urena M. Tetrahedron 65 (2009) 3757-3766
14. Viso A., Fernandez de la Pradilla R., Flores A., and Garcia A. Tetrahedron 63 (2007) 8017-8026 and references cited therein
15. Viso A., Fernandez de la Pradilla R., Flores A., Garcia A., Tortosa M., and Lopez-Rodrigez M.L. J. Org. Chem. 71 (2006) 1442-1448
16. For an asymmetric synthesis of the (+)-(2R,3S) isomer of CP-99,994 see:. Ahari M., Perez A., Menant C., Vasse J.-L., and Szymoniak J. Org. Lett. 10 (2008) 2473-2479
17. Viso A., Fernandez de la Pradilla R., Lopez-Rodrigez M.L., Garcia A., Flores A., and Alonso M. J. Org. Chem. 69 (2004) 1542-1547
18. Blakemore P.R., Kocienski P.J., Morley A., and Muir K.J. J. Chem. Soc., Perkin Trans. 1 (1999) 955-968
19. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168-8179
20. For a review see:. Felpin F.-X., and Lebreton J. Curr. Org. Syn. 1 (2004) 83-109
21. For leading references see:. Davis F.A., Xu H., and Zhang J. J. Org. Chem. 72 (2007) 2046-2052
22. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
23. 20 -78 (c 1.0, MeOH)].
24. Desai M.C., Lefkowitz S.L., Thadeio P.F., Longo K.P., and Snider R.M. J. Med. Chem. 35 (1992) 4911-4913