Asymmetric synthesis using a new chiral β-functionalized allylboronate derived from endo-2-phenyl-exo-2,3-bornanediol: Preparation and reactions with aldehydes.

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3719-3722

  Chataigner, Isabelle ^a   Lebreton, Jacques ^a   Zammattio, Fraņoise ^a   Villiéras, Jean ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030902539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00708-9     Document Type: Article

References (15)

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3. Portions of this work are described in : Nyzam, V.; Ph.D. Thesis, Nantes Faculty of Science, France, 1996.
4. (a) Herold, T.; Schrott, U.; Hoffmann, R.W.; Chem. Ber., 1981, 114, 359-374.
5. (b) Hoffmann, R.W.; Herold, T.; Chem. Ber., 1981, 114, 375-383.
6. Schmid, C.R.; Bradley, D.A.; Synthesis, 1992, 587-590.
7. Herold, T.; Hoffmann, R.W.; Angew. Chem., Int. Ed. Engl., 1978, 17, 768-769.
8. Hoffmann, R.W.; Endesfelder, A.; Zeiss, H.J.; Carbohydrate Res., 1983,123, 320-325.
9. Trost, B.M.; Belletire, J. L.; Godleski, S.; Mc Dougal, P.G.; Balkorec, M; Baldwin, J.J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P.; J. Org. Chem., 1986, 51, 2370-2374.
10. Roush, W.R.; Banfi, L.; J. Am. Chem. Soc, 1988, 110, 3979-3989.
11. Corey, E. J.; Rohde, J. F.; Fisher, A.; Azimioara, M.D., Tetrahedron Lett, 1997, 38, 33-36 and the following paper.
12. (a) Roush, W.R.; Walts, A.E.; Tetrahedron Lett., 1985, 20, 3427-3430.
13. (b) Roush, W.R.; Adam, M.A.; Harris, D.J.; J. Org. Chem., 1985, 50, 2000-2003.
14. (c) Mulzer, J.; Angermann, A.; Tetrahedron Lett., 1983, 24, 2843-2846.
15. 3) δ (ppm): 9.3 ; 13.8 ; 17.1 ; 20.7 ; 23.5 ; 24.6 ; 29.5 ; 48.7 ; 50.1 ; 51.9 ; 60.4 ; 88.7 ; 95.7 ; 124.0 ; 126.6 ; 127.1 ; 127.3 ; 137.3 ; 141.6 ; 167.2 MS m/e (I%) : 368 (1) ; 258 (100) ; 230 (28) ; 162 (19) ; 141 (34) ; 105(21) ; 95 (19) ; 68 (23) ; 29 (14).