The threo-selective reaction of but-2-enyl organometallic compounds with ethylidenemalonates and related compounds

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 7, 1985, Pages 386-388

  Yamamoto, Yoshinori ^a   Nishii, Shinji ^a   Maruyama, Kazuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049097418     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39850000386     Document Type: Article

References (13)

1. For example, Tetrahedron Symp, No. 16, ed. T. Mukaiyama, 1984, vol. 40, and references cited therein.
2. The previous methods for this stereocontrol are primarily based on intramolecular reactions, such as ester enolate and thio Claisen rearrangements. For example, see R. E. Ireland andM. D. Varney, J. Am. Chem. Soc., 1984, 106, 3668.
3. Y. Tamaru, Y. Furukawa, M. Mizutani, O. Kitao, and Z. Yoshida, J. Org. Chem., 1983, 48, 3631.
4. P. Beslin, P. Metzner, Y. Vallée, and J. Vialle, Tetrahedron Lett., 1983, 3617.
5. For faranal, see R. Baker, D. C. Billington, and N. Ekanayake, J. Chem. Soc., Perkin Trans. 1, 1983, 1387.
6. D. W. Knight and A. Ojhara, Tetrahedron Lett., 1981, 5101.
7. Forikarugamycin, see M. J. Kurth, D. H. Burns, andM. J. O’Brien, J. Org. Chem., 1984, 49, 733.
8. For steroid side chains, see T. Gebreyesus and C. Djerassi, Tetrahdron Lett., 1982, 4427.
9. Y. Yamamoto and K. Maruyama, Heterocycles, 18, 1982, 357 and references cited therein.
10. For the reaction of isopropylidenemalonates with Grignard reagents, see G. A. Holmberg and R. Sjoholm, Acta. Chem. Scand., 1970, 24, 3490.
11. Y. Yamamoto and K. Maruyama, Heterocycles, 18, 1982, 357 and references cited therein.
12. N. L. Allinger, J. Am. Chem. Soc., 1959, 81, 5727.
13. D. El-abed, A. Jellal, and M. Santelli, Tetrahedron Lett., 1984, 1463.