A synthesis of multisubstituted vinylsilanes via ynolates: Stereoselective formation of β-silyl-β-lactones followed by decarboxylation

Chemical Communications

Volumn , Issue 19, 2005, Pages 2477-2479

  Shindo, Mitsuru ^a   Matsumoto, Kenji ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BETA SILYL BETA LACTONE DERIVATIVE; BETA SILYL BETA LACTONE ENOLATE DERIVATIVE; LACTONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; CYCLOADDITION; DECARBOXYLATION; DIASTEREOISOMER; GEOMETRY; OLEFINATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; REPRODUCIBILITY; RING OPENING; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOISOMERISM; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 20044380935     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418310j     Document Type: Article

References (21)

1. For recent reviews, see: (a) I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063;
2. (b) M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
3. (a) J. A. Soderquist and C. L. Anderson, Tetrahedron Lett., 1988, 29, 2425;
4. (b) G. L. Larson, J. A. Soderquist and M. R. Claudio, Synth. Commun., 1990, 20, 1095;
5. (c) P. Jankowski, K. Plesniak and J. Wicha, Org. Lett., 2003, 5, 2789.
6. M. Shindo, K. Matsumoto, S. Mon and K. Shishido, J. Am. Chem. Soc., 2002, 124, 6840.
7. For reviews, see: (a) M. Shindo, Synthesis, 2003, 2275;
8. (b) M. Shindo, J. Synth. Org. Chem. Jpn., 2000, 58, 1155;
9. (c) M. Shindo, Yakugaku Zasshi, 2000, 120, 1233;
10. (d) M. Shindo, Chem. Soc. Rev., 1998, 27, 367.
11. W. Adam and L. A. A. Encarnacion, Synthesis, 1979, 388.
12. Some of the β-lactones can be purified by recrystallization to remove minor isomers.
13. Acylsilanes were prepared from silyl thioacetals, like 2-silyl-1,3-dithianes. See ESI.
14. 1H-NMR spectrum.
15. K. Utimoto, M. Kitai and H. Nozaki, Tetrahedron Lett., 1975, 2825.
16. For a review, see: A. Pommier and J.-M. Pons, Synthesis, 1993, 441.
17. (a) M. Shindo, Y. Sato and K. Shishido, J. Am. Chem. Soc., 1999, 121, 6507
18. (b) See, also: R. L. Danheiser and J. S. Nowick, J. Org. Chem., 1991, 56, 1176;
19. (c) J. Mulzer and A. Chucholowski, Angew. Chem., Int. Ed Engl., 1982, 21, 777.
20. R. A. N. C. Crump, I. Fleming, J. H. M. Hill, N. L. Reddy and D. Waterson, J. Chem. Soc., Perkin Trans. 1, 1992, 3277.
21. B. M. Trost, M. R. Machacek and Z. T. Ball, Org. Lett., 2003, 5. 1895.