Highly stereocontrolled synthesis of substituted propiolactones and butyrolactones from achiral lithium enolates and homochiral aldehydes

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 245-248

  Arrastia, Iosune ^a   Lecea, Begoña ^b   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b Farmazi Fakultatea   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; PROPIOLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030035026     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02139-6     Document Type: Article

References (21)

1. (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
2. (b) Oligaruso, M.A.: Wolfe, J.F. Synthesis of Lactones and Lactams. Patai, S.; Rappoport, Z., Eds. Wiley: Chichester, 1993 (pp 3-131).
3. (a) Danheiser, R.L.; Nowick, J.S. J.Org.Chem. 1991, 56, 1176.
4. (b) Danheiser, R.L.; Choi, Y.M.; Menichincheri, M.; Stoner, E.J. J.Org.Chem. 1993, 58, 322.
5. 3) δ 174.4, 110.2, 80.7, 73.8, 67.1, 54.2, 27.0, 25.1, 22.6, 16.4.
6. It is well known that this reaction takes place with double inversion of configuration for the two stationary carbon atoms, See for example: (a) Recta, M.T.; Schmitz, A.; Holdgrān, X. Tetrahedron Lett. 1989, 30, 5421.
7. (b) Mulzer, J.; Brütrup, G. Angew.Chem. Int. Ed. Engl. 1979, 18, 793.
8. (c) Black, T.H.; Hall, J.A.; Sheu, R.G. J.Org.Chem. 1998, 53, 2371.
9. Stewart, J.J.P. J.Comput.Chem. 1989, 10, 209.
10. Anders, E.; Koch, R.; Freunscht, P. J.Comput.Chem. 1993, 14, 1301.
11. (a) Bürgi, H.B.; Lehn, J.M.: Wipff, G. J.Am.Cnem.Soc. 1974, 96, 1956.
12. (b) Bürgi, H.B.; Dunitz, J.D.; Lehn, J.-M. Tetrahedron 1974, 30, 1563.
13. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199.
14. (b) Anh, N.T.; Eisestein, O. Nouv.J.Chim. 1977, 1, 61.
15. Black, T.H.; DuBay III, W.J.; Tully, P.S. J.Org.Chem. 1988, 53, 5922.
16. A related observation on the dependence of the migrating group with the Lewis acid has recently been reported by Mulzer. See Mulzer, J.; Pointner, A.; Straßer, R.; Hoyer, K.; Nagel, V. Tetrahedron Lett. 1995, 36, 3679.
17. 3) δ 179.7, 137.3, 128.6, 128.2, 127.7, 88.4, 76.6, 73.2, 43.8, 24.3, 18.9, 18.5.
18. See for example: (a) Toshima, H.; Goto, T.; Ichihara, A. Tetrahedron Lett. 1995, 36, 3373.
19. (b) Takanata, H.: Uchida, Y.; Momose, T. J.Org.Chem. 1994, 59, 7201.
20. Reetz has observed in situ dyotropic rearrangement in aldol reactions using N,N-dibenzyl-α-aminoaldehydes, see ref. 4a
21. 3) δ 180.8, 138.7, 128.5, 128.4, 127.3, 73.7, 73.5, 69.2, 43.8, 25.6, 21.1, 19.9.