3-Benzyloxy-1-isocyanopropenes. Synthesis and use as 3-hydroxypropanoyl anion equivalents

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2437-2440

  Kobayashi, Kazuhiro ^a   Akamatsu, Hideki ^a   Takada, Keiichiro ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029932781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00312-7     Document Type: Article

References (26)

1. For an excellent review of acyl anion equivalents, see Ager, D. J. In Umpoled Synthons; Hase, T. A. Ed.; Wiley: New York, 1987; p. 19.
2. For reports concerning on acyl anion equivalents bearing a functional group, see Carlson, R. M.; Isidor, T. L. Tetrahedron Lett., 1973, 4819; Carlson, R. M; Jones, R. W.; Hatcher, A. S. Tetrahedron Lett., 1975, 1741; Murakami, M.; Kawano, T.; Ito, Y. J. Am. Chem. Soc., 1990, 112, 2437.
3. For reports concerning on acyl anion equivalents bearing a functional group, see Carlson, R. M.; Isidor, T. L. Tetrahedron Lett., 1973, 4819; Carlson, R. M; Jones, R. W.; Hatcher, A. S. Tetrahedron Lett., 1975, 1741; Murakami, M.; Kawano, T.; Ito, Y. J. Am. Chem. Soc., 1990, 112, 2437.
4. For reports concerning on acyl anion equivalents bearing a functional group, see Carlson, R. M.; Isidor, T. L. Tetrahedron Lett., 1973, 4819; Carlson, R. M; Jones, R. W.; Hatcher, A. S. Tetrahedron Lett., 1975, 1741; Murakami, M.; Kawano, T.; Ito, Y. J. Am. Chem. Soc., 1990, 112, 2437.
5. 5 by the standard acetalization procedure.
6. Sheeham, J. C.; Goodman, M.; Richardson, L. J. Am. Chem. Soc., 1955, 77, 6391.
7. Manzocchi, A.; Fiecchi, A.; Santaniello, E. Synthesis, 1987, 1007.
8. 13NO: M, 187.0997.
9. Schoellkopf, U. Angew. Chem. Int. Ed. Engl., 1977, 16, 339. Lithiation of vinyl isocyanides with butyllithium and reactions of the resulting vinyllithium compounds with electrophiles have been reported previously; Schoellkopf, U.; Staffurst, D.; Jentsch, R. Liebigs Ann. Chem., 1977, 1167.
10. Schoellkopf, U. Angew. Chem. Int. Ed. Engl., 1977, 16, 339. Lithiation of vinyl isocyanides with butyllithium and reactions of the resulting vinyllithium compounds with electrophiles have been reported previously; Schoellkopf, U.; Staffurst, D.; Jentsch, R. Liebigs Ann. Chem., 1977, 1167.
11. 15NO: M, 201.1154.
12. 2: M, 220.1464.
13. 2: M, 164.0838.
14. a) Martin ,V. A.; Albizati, K. F. J. Org. Chem., 1988, 53, 5986;
15. b) J. Am. Chem. Soc., 1990, 112, 6965;
16. c) Hitchcock, S. R.; Perron, F.; Martin, V. A.; Albizati, K. F. Synthesis, 1990, 1059.
17. E.g., inter alia: a) Martin, V. A.; Perron, F.; Albizati, K. F. Tetrahedron Lett., 1990, 31, 301;
18. b) Cottier, L.; Descotes, G.; Grenier, M. F.; Metras, F. Tetrahedron, 1981, 37, 2515;
19. c) White, J. D.; Carter, J. P.; Kezar, III, H. S. J. Org. Chem., 1982, 47, 929.
20. a) Hoffmann, C. H.; Wagner, A. F.; Wilson, A. N.; Walton, E.; Shunk, C. H.; Wolf, D. E.; Holly, F. W.; Folkers, K. J. Am. Chem. Soc., 1957, 79, 2316;
21. b) Tsuji, J.; Nagashima, H.; Hori, K. Tetrahedron Lett., 1982, 23, 2679.
22. For syntheses of these derivatives based on methods other than aldol-type processes, see refs. 11c and 16b, and references cited therein.
23. a) Hays, J. T.; Hager, G. F.; Engelmann, H. M.; Spurlin, H. M. J. Am. Chem. Soc., 1951, 73, 5369;
24. b) Santelli, M.; Viala, J. Tetrahedron, 1978, 34, 2327.
25. a) Koulkes, M. Bull. Soc. Chim. Fr., 1957, 127;
26. b) Molander, G. A.; Hahn, G. J. Org. Chem., 1986, 51, 2596.