Microwave-assisted aminolysis of vinylepoxides

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9273-9276

  Lindström, Ulf M ^a   Olofsson, Berit ^a   Somfai, Peter ^b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Aminoalcohols; Aminolysis; Microwave heating; Ring opening; Vinylepoxides

Indexed keywords

AMINOALCOHOL; AMMONIUM DERIVATIVE; EPOXIDE;

ARTICLE; LYSIS; MICROWAVE IRRADIATION; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033601464     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01811-0     Document Type: Article

References (13)

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12. The relative configuration of each aminoalcohol was determined by conversion into the corresponding oxazolidinone or aziridine. The trans-vinylaziridines obtained from anti-aminoalcohols showed J=2.3-2.6 Hz and the cis-oxazolidinones prepared from the same precursors had J=7.8-8.1 Hz, which is in accordance with the assigned structures. See: Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. J. Org. Chem. 1996, 61, 2677-2685, and Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of Spectral Data for Structure Determination of Organic Compounds; Springer: Berlin, 1989. The relative configuration of compound 2d was determined by NOE experiments on the corresponding oxazolidinone.
13. The relative configuration of each aminoalcohol was determined by conversion into the corresponding oxazolidinone or aziridine. The trans-vinylaziridines obtained from anti-aminoalcohols showed J=2.3-2.6 Hz and the cis-oxazolidinones prepared from the same precursors had J=7.8-8.1 Hz, which is in accordance with the assigned structures. See: Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. J. Org. Chem. 1996, 61, 2677-2685, and Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of Spectral Data for Structure Determination of Organic Compounds; Springer: Berlin, 1989. The relative configuration of compound 2d was determined by NOE experiments on the corresponding oxazolidinone.