Allyltrichlorostannane additions to chiral aldehydes

Tetrahedron Letters

Volumn 44, Issue 36, 2003, Pages 6861-6866

  Dias, Luiz Carlos ^a   Dos Santos, Débora Ribeiro ^a   Steil, Leonardo José ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; TIN DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; STEREOCHEMISTRY;

EID: 0042660831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01713-1     Document Type: Article

References (40)

1. Fleming I., Barbero A., Walter D. Chem. Rev. 97:1997;2063.
2. Nishigaichi Y., Takuwa A., Naruta Y., Maruyama K. Tetrahedron. 49:1993;7395.
3. Panek J.S., Xu F., Rondon A.C. J. Am. Chem. Soc. 120:1998;4113.
4. Zhu B., Panek J.S. Eur. J. Org. Chem. 9:2001;1701.
5. Huang H.B., Spande T.F., Panek J.S. J. Am. Chem. Soc. 125:2003;626.
6. Keck G.E., Abbott D.E. Tetrahedron Lett. 25:1984;1883.
7. Trost B.M., Urabe H. J. Org. Chem. 55:1990;3982.
8. Nishigaishi Y., Takuwa A., Jodai A. Tetrahedron Lett. 32:1991;2383.
9. Almendros P., Gruttadauria M., Helliwell M., Thomas E.J. J. Chem. Soc., Perkin Trans. 1. 1997;2549.
10. Deka D.C., Helliwell M., Thomas E.J. Tetrahedron. 57:2001;10017.
11. Martin N., Thomas E.J. Tetrahedron Lett. 42:2001;8373.
12. Kumar P., Thomas E.J., Tray D.R. J. Braz. Chem. Soc. 12:2001;623.
13. Dias L.C., Giacomini R. J. Braz. Chem. Soc. 9:1998;357.
14. Evans D.A., Coleman P.J., Dias L.C. Angew Chem., Int. Ed. Engl. 36:1997;2738.
15. Evans D.A., Trotter B.W., Cote B., Coleman P.J., Dias L.C., Tyler A.N. Angew Chem., Int. Ed. Engl. 36:1997;2744.
16. Dias L.C., Giacomini R. Tetrahedron Lett. 39:1998;5343.
17. Dias L.C., Meira P.R.R., Ferreira E. Org. Lett. 1:1999;1335.
18. Dias L.C., Meira P.R.R. Synlett. 2000;37.
19. Dias L.C., Ferreira E. Tetrahedron Lett. 42:2001;7159.
20. Dias L.C., Ferreira A.A., Diaz G. Synlett. 2002;1845.
21. Dias L.C., Diaz G., Ferreira A.A., Meira P.R.R., Ferreira E. Synthesis. 4:2003;603.
22. We have recently described a very efficient and synthetically useful 1,4-anti-1,5-anti boron-mediated aldol reaction of chiral α-methyl-β-alkoxy methyl ketone with achiral aldehydes: Dias L.C., Baú R.Z., de Sousa M.A., Zukerman-Schpector J. Org. Lett. 4:2002;4325.
23. Bunnelle W.H., Narayanan B.A. Tetrahedron Lett. 28:1987;6261.
24. Mickelson T.J., Koviach J.L., Forsyth C.J. J. Org. Chem. 61:1996;9617.
25. Gage J.R., Evans D.A. Org. Synth. 68:1990;83.
26. Evans D.A., Bartroli J., Shih T.L. J. Am. Chem. Soc. 103:1981;2127.
27. Evans D.A., Taber T.R. Tetrahedron Lett. 21:1980;4675.
28. Evans D.A., Downey C.W., Shaw J.T., Tedrow J.S. Org. Lett. 4:2002;1127.
29. Since the diastereoselectivity of the reactions of these aldehydes with allyltrichlorostannanes 3 and 6 depends on their enantiomeric purity, crude aldehydes were used in all of the studies described in the text.
30. Schreiber S.L., Shambayati S., Blake J.F., Wierschke S.G., Jorgensen W.L. J. Am. Chem. Soc. 112:1990;697.
31. Evans D.A., Dart M.J., Duffy J.L., Yang M.G. J. Am. Chem. Soc. 118:1996;4322.
32. 13C NMR spectroscopic analysis of the purified product mixture The syn and anti-products could not be separated and were characterized as mixtures. We have been able to separate both syn and anti diols originating from homoallylic alcohols 18 and 24 and they were characterized individually All of the percentage values represent data obtained from three individual trials.
33. Having confirmed the relative (syn or anti) relationship between allylsilane derived stereogenic centers, the absolute stereochemistry of the newly formed hydroxyl substituent was determined by ascertaining its relationship to the stereocenter originating from the aldehydes, which are of known configuration.
34. Rychnovsky S.D., Skalitzky D.J. Tetrahedron Lett. 31:1990;945.
35. Evans D.A., Rieger D.L., Gage J.R. Tetrahedron Lett. 31:1990;7099.
36. Rychnovsky S.D., Rogers B.N., Richardson T.I. Acc. Chem. Res. 31:1998;9.
37. Chérest M., Felkin H., Prudent N. Tetrahedron Lett. 18:1968;2199.
38. Anh N.T., Eisenstein O. Nouv. J. Chem. 1:1977;61 We use the 'Felkin' descriptor to refer to the diastereomer predicted by the Felkin-Ahn paradigm. The 'anti-Felkin' descriptor refers to diastereomers not predicted by this transition state model.
39. 13C NMR, IR, MS, and HRMS spectral data.
40. 4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (30% EtOAc/hexanes) gave the corresponding homoallylic alcohols.