Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation

Tetrahedron

Volumn 65, Issue 28, 2009, Pages 5541-5551

  Robertson, Jeremy ^a   Hall, Michael J ^b   Green, Stuart P ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; HYDROXYL GROUP;

ALLYLATION; ALPHA METHALLYLATION; ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; ENERGY; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 66349097118     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.117     Document Type: Article

References (37)

1. Robertson J., Hall M.J., Stafford P.M., and Green S.P. Org. Biomol. Chem. 1 (2003) 3758-3767
2. For pertinent descriptions of carbonyl ene cyclisations containing discussion of stereochemistry and mechanism under a variety of conditions, see:
3. Williams J.T., Bahia P.S., and Snaith J.S. Org. Lett. 4 (2002) 3727-3730
4. Kocovsky P., Ahmed G., Srogl J., Malkov A.V., and Steele J. J. Org. Chem. 64 (1999) 2765-2775
5. Snider B.B., Karras M., Price R.T., and Rodini D.J. J. Org. Chem. 47 (1982) 4538-4545
6. Robertson J., Hall M.J., and Green S.P. Org. Biomol. Chem. 1 (2003) 3635-3638
7. Review:. Jones G.R., and Landais Y. Tetrahedron 52 (1996) 7599-7662
8. Blackwell J.M., Foster K.L., Beck V.H., and Piers W.E. J. Org. Chem. 64 (1999) 4887-4892
9. See also. Gevorgyan V., Rubin M., Benson S., Liu J.-X., and Yamamoto Y. J. Org. Chem. 65 (2000) 6179-6186
10. Rajagopalan S., and Zweifel G. Synthesis (1984) 113-115
11. Prepared by the general procedure described in. Rajagopalan S., and Zweifel G. Synthesis (1984) 111-112
12. See Experimental section for details.
13. E.g., by the deprotonation and silylation of E-but-2-ene:. Knölker H.-J., Baum E., and Schmitt O. Tetrahedron Lett. 39 (1998) 7705-7708
14. Hodgson D.M., Barker S.F., Mace L.H., and Moran J.R. Chem. Commun. (2001) 153-154
15. Matsuda I., Kato T., Sato S., and Izumi Y. Tetrahedron Lett. 27 (1986) 5747-5750
16. Kahle K., Murphy P.J., Scott J., and Tamagni R. J. Chem. Soc., Perkin Trans. 1 (1997) 997-999
17. Kim C., Choi S.K., Park E., and Jung I. J. Korean Chem. Soc. 41 (1997) 88-97
18. Meerpoel L., and Hoornaert G. Synthesis (1990) 905-908 and references cited therein
19. Hayashi M., Yoshiga T., Nakatani K., Ono K., and Oguni N. Tetrahedron 50 (1994) 2821-2830
20. Cf. Jafarpour L., Heck M.-P., Baylon C., Lee H.M., Mioskowski C., and Nolan S.P. Organometallics 21 (2002) 671-679
21. 1H NMR experiment was processed automatically within MestRe-C using a set of preset parameters followed by automated integration of the methine signals.
22. -1), see:. Oppolzer W., and Snieckus V. Angew. Chem., Int. Ed. Engl. 17 (1978) 476-486
23. Spartan'06, Wavefunction, Irvine, CA:. Shao Y., Molnar L.F., Jung Y., Kussmann J., Ochsenfeld C., Brown S.T., Gilbert A.T.B., Slipchenko L.V., Levchenko S.V., O'Neill D.P., DiStasio Jr. R.A., Lochan R.C., Wang T., Beran G.J.O., Besley N.A., Herbert J.M., Lin C.Y., Van Voorhis T., Chien S.H., Sodt A., Steele R.P., Rassolov V.A., Maslen P.E., Korambath P.P., Adamson R.D., Austin B., Baker J., Byrd E.F.C., Dachsel H., Doerksen R.J., Dreuw A., Dunietz B.D., Dutoi A.D., Furlani T.R., Gwaltney S.R., Heyden A., Hirata S., Hsu C.-P., Kedziora G., Khalliulin R.Z., Klunzinger P., Lee A.M., Lee M.S., Liang W.Z., Lotan I., Nair N., Peters B., Proynov E.I., Pieniazek P.A., Rhee Y.M., Ritchie J., Rosta E., Sherrill C.D., Simmonett A.C., Subotnik J.E., Woodcock III H.L., Zhang W., Bell A.T., Chakraborty A.K., Chipman D.M., Keil F.J., Warshel A., Hehre W.J., Schaefer H.F., Kong J., Krylov A.I., Gill P.M.W., and Head-Gordon M. Phys. Chem. Chem. Phys. 8 (2006) 3172-3191
24. Matsumoto K., Oshima K., and Utimoto K. J. Org. Chem. 59 (1994) 7152-7155
25. For a summary of aspects of stereocontrol involving reactions between aldehydes and allylsilane derivatives, see pp 2112-2118 in. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063-2192
26. Robertson J., Stafford P.M., and Bell S.J. J. Org. Chem. 70 (2005) 7133-7148
27. 29Si NMR (employing a refocussed INEPT experiment), however no evidence of a pre-coordinated intermediate was observed.
28. Kobayashi S., and Nishio K. J. Org. Chem. 59 (1994) 6620-6628
29. Hosomi A., Kohra S., Ogata K., Yanagi T., and Tominaga Y. J. Org. Chem. 55 (1990) 2415-2420
30. Kira M., Hino T., and Sakurai H. Tetrahedron Lett. 30 (1989) 1099-1102
31. Kira M., Sato K., and Sakurai H. J. Am. Chem. Soc. 110 (1988) 4599-4602
32. Kira M., Kobayashi M., and Sakurai H. Tetrahedron Lett. 28 (1987) 4081-4084
33. For a theoretical study, see:. Omoto K., Sawada Y., and Fujimoto H. J. Am. Chem. Soc. 118 (1996) 1750-1755
34. See, for example. Zacuto M.J., O'Malley S.J., and Leighton J.L. J. Am. Chem. Soc. 124 (2002) 7890-7891
35. Roberts T.G., and Teague P.C. J. Am. Chem. Soc. 77 (1955) 6258-6261
36. Hartwig W., and Schöllkopf U. Liebigs Ann. Chem. (1982) 1952-1970
37. Bessard Y., and Crettaz R. Tetrahedron 56 (2000) 4739-4745