The reaction of allenes with phosphorus(III) compounds bearing a P-NH-(t-Bu) group: isolation of both enantiomers in crystalline form from an achiral system

Tetrahedron Letters

Volumn 49, Issue 50, 2008, Pages 7135-7138

  Bhuvan Kumar, N N ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AMPHOLYTE; CYCLODIPHOSPHAZANE; PHOSPHINE DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS;

EID: 54449101617     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.153     Document Type: Article

References (30)

1. Lu X., Zhang C., and Xu Z. Acc. Chem. Res. 34 (2001) 535-544 (phosphine catalysis)
2. Valentine Jr. D.H., and Hillhouse J.H. Synthesis (2003) 317-334
3. Nair V., Rajesh C., Vinod A.U., Bindu S., Sreekanth A.R., Mathen J.S., and Balagopal L. Acc. Chem. Res. 36 (2003) 899-907 (multicomponent reactions involving phosphines)
4. Selected references:. Luis A.L., and Krische M.J. Synthesis (2004) 2579-2585
5. Hanédanian M., Loreau O., Taran F., and Mioskowski C. Tetrahedron Lett. 45 (2004) 7035-7038
6. Kuroda H., Hanaki E., Izawa H., Kano M., and Itahashi H. Tetrahedron 60 (2004) 1913-1920
7. Xu L.-W., and Xia C.-C. Tetrahedron Lett. 45 (2004) 4507-4510
8. Lu C., and Lu X. Tetrahedron 60 (2004) 6575-6579
9. Koech P.K., and Krische M.J. J. Am. Chem. Soc. 126 (2004) 5350-5351
10. Gimbert C., Lumbierres M., Marchi C., Moreno-Mañas M., Sebastián R.M., and Vallribera A. Tetrahedron 61 (2005) 8598-8605
11. Tebby J.C., Wilson I.F., and Griffiths D.V. J. Chem. Soc., Perkin Trans. 1 (1979) 2133-2135 and references cited therein
12. Aitken R.A., Costello S.J., Slawin A.M.Z., and Wilson N.J. Eur. J. Org. Chem. (2003) 623-625
13. Nuyken, O. Polymers of acrylic acid, methacrylic acid, maleic acid and their derivatives. In Handbook of Polymer Synthesis, 2nd ed.; Kricheldorf, H. R., Nuyken, O., Swift, G., Eds.; Marcel Dekker: New York, 2005, pp 241-332.
14. Nair V., Sreekanth A.R., and Vinod A.U. Org. Lett. 3 (2001) 3495-3497
15. Li C.-Q., and Shi M. Org. Lett. 5 (2003) 4273-4276
16. Ding H., Ma C., Yang Y., and Wang Y. Org. Lett. 7 (2005) 2125-2127
17. Islami M.R., Mollazehi F., Badiei A., and Sheibani H. ARKIVOC XV (2005) 25-29
18. Bhuvan Kumar N., Manab Chakravarty N., and Kumara Swamy K.C. New J. Chem. 30 (2006) 1614-1620
19. +. X-ray structure was determined for this compound. The enantiomeric forms were detected using the CD spectra as an indicator.
20. Allene preparation: Satish Kumar, N. Studies on the Synthesis, Reactivity and Utility of Cyclic Phosphorus(III) Compounds and Organophosphonates, Ph.D. thesis, University of Hyderabad: India, 2004.
21. Guillemin J.C., Savignac P., and Denis J.M. Inorg. Chem. 30 (1991) 2170
22. Lang, R. W.; Hansen, H.-J. Organic Syntheses, Coll. Vol. 7, p. 232.
23. 2: C, 57.37; H, 10.07; N, 12.16. Found: C, 57.46; H, 10.05; N, 12.08.
24. 2 (all data) = 0.1015. Flack parameter: -0.03(8). CCDC 697363.
25. Sheldrick G.M. sadabs Siemens Area Detector Absorption Correction (1996), University of Göttingen, Germany
26. Sheldrick, G. M. shelxtl nt Crystal Structure Analysis Package, Bruker AXS, Analytical X-ray System, WI, USA, 1999, version 5.10.
27. Pérez-Garcíaa L., and Amabilino D.B. Chem. Soc. Rev. 36 (2007) 941-967
28. Jayanty S., and Radhakrishnan T.P. Chem. Eur. J. 10 (2004) 2661-2667 this paper refers to conformationally chiral molecules) and references 7-9 cited therein
29. Raghavaiah P., Supriya S., and Das S.K. Chem. Commun. (2006) 2762-2764
30. 2C{double bond, long}CHR [R = electron withdrawing group] with 6. Full characterization data are available from us. {A figure is presented}