A convenient synthesis of 3-iodohomoallylic alcohols and the further transformation to α,β-unsaturated γ-lactones

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4831-4834

  Zhang, Chunming ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; GAMMA LACTONE DERIVATIVE; IODIDE ION;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030960037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01047-2     Document Type: Article

References (13)

1. Landor, S. R. Nucleophilic addition to allenes. In The Chemistry of the Allenes; Landor, S. R. Ed.; Academic Press: London, 1982; vol. 2, pp 361-397.
2. Padwa, A.; Yeske, P. E. J. Org. Chem. 1991, 56, 6386-6390.
3. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908.
4. 4) and evaporated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (petroleum ether/ethyl acetate = 10 : 1) to give syn-3a (110 mg) and anti-3a (110 mg).
5. 2I (310.17): C, 42.60; H, 6.17. Found: C, 42.30; H, 5.86.
6. Galatsis, P.; Millan, S. D.; Nechala, P.; Ferguson, G. J. Org. Chem. 1994, 59, 6643-6651 and references cited therein.
7. Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630-3633. Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058-4067.
8. Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630-3633. Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058-4067.
9. Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed Engl. 1985, 24, 94-110. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157-183.
10. Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed Engl. 1985, 24, 94-110. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157-183.
11. Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193-4198.
12. 4), and concentrated. The residue was puried by chromatography on silica gel (petroleum ether/ethyl acetate = 5 : 1) to give the carbonylated product 4 (185 mg, 88%).
13. 3 (210.27): C, 68.55; H, 8.62. Found: C, 68.30; H, 8.52.