Synthesis of Different Chiral Amino γ-Butyrolactones and Amino γ-Butenolides

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1303-1305

  Concellón, José M ^a   Riego, Estela ^a   Bernad, Pablo L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GAMMA BUTYROLACTONE;

ARTICLE; CONFORMATION; HYDROLYSIS; SYNTHESIS;

4-BUTYROLACTONE; HYDROLYSIS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION;

EID: 0037129396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0255918     Document Type: Article

References (22)

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15. 4), filtered, and concentrated in vacuo. Flash column chromatography (silica gel, hexane:ethyl acetate = 5:1) provided pure compound 2.
16. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247-1251.
17. 4), filtered, and concentrated in vacuo. Flash column chromatography (silica gel, hexane: ethyl acetate = 5:1) provided pure compound 6.
18. Formation of azetidinium salts starting from halohydrins has been also observed in similar substrates: (a) Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. J. Org. Chem. 1997, 62, 8902-8906. (b) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1997, 62, 5974-5977. (c) Reference 4.
19. Formation of azetidinium salts starting from halohydrins has been also observed in similar substrates: (a) Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. J. Org. Chem. 1997, 62, 8902-8906. (b) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1997, 62, 5974-5977. (c) Reference 4.
20. Formation of azetidinium salts starting from halohydrins has been also observed in similar substrates: (a) Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. J. Org. Chem. 1997, 62, 8902-8906. (b) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1997, 62, 5974-5977. (c) Reference 4.
21. A similar opening-closing process has been observed in aminoiodohydrins previously: Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. Tetrahedron Lett. 2000, 62, 1231-1234.
22. 4), filtered, and concentrated in vacuo. Flash column chromatography over silica gel (hexane:ethyl acetate = 15:1) provided pure compounds 8.