Catalytic synthesis of allenes via isomerization of alkynes under phase- transfer catalyzed conditions

Synlett

Volumn , Issue 4, 2000, Pages 493-494

  Oku, Makoto ^a   Arai, Shigeru ^a   Katayama, Kimiko ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Allenes; Asymmetric reactions; Catalysts; Isomerization; Phase transfer

Indexed keywords

ALKYNE; ALLENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ISOMERISM; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0034033893     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. PTC reviews, see a) Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Trasnsfer Catalysis. Fundamentals, Applications, and Industrial Perpectives: Chapman & Hall: New York 1994.
2. b) Halpern, M.E., Ed. Phase-Transfer Catalysis. Mechanism and Synthesis; American Chemical Society: Washington DC 1997.
3. c) Sasson, Y.; Neumann, R., Ed. Handbook of Phase Transfer Catalysis; Blackie A. & M.: London 1997.
4. d) Tavener, S. J.; Clark, J. H. Chemistry & Industry 1997, 22.
5. Recently, we have published some successful results for PTC catalyzed asymmetric reactions, see: a) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145.
6. b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563.
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13. For recent succesful examples of PTC catalyzed asymmetric reactions, see: a) Lygo, B.; Wainwrite, P. G. Tetrahedron Lett. 1998, 39, 1599.
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18. An allene was obtained as a by-product by isomerization of an alkyne under PTC conditions, see: Dou, H. J.; Elguero, J.; Espada, M.; Hassanaly, P. Anal. Quim. 1978, 74, 1137.
19. For reviews of allenyl compounds, see: a) Lander, S. R. The Chemistry of Allenes; Academic Press: New York 1982.
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21. c) Pasto, D. J. Tetrahedron 1984, 40, 2805. For the recent synthetic approach to racemic allenyl compounds, see:
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25. b) Michel, P.; Gennet, D.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575, and references cited therein.
26. 3) δ ppm: 97.6, 98.9, 121.0, 127.0, 127.5, 128.5, 128.8, 130.2, 131.4, 131.8, 132.7, 133.2, 207.9.
27. This chiral PTC is quite effective in asymmetric cyclopropanation. See ref 2g.
28. For reviews of chiral allenyl compounds, see: a) Rossi, R.; Diversi, P. Synthesis 1973, 25.
29. b) Smadia, W. Chem. Rev. 1983, 83, 263.