Synthesis of enantiomerically pure 2,3-disubstituted oxirane-2- carboxamides

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3503-3511

  García Ruano, José L ^a   Martín Castro, Ana M ^a   Rodríguez Ramos, Jesús H ^a   Rubio Flamarique, Ana C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ETHYLENE OXIDE DERIVATIVE;

CYCLIZATION; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 0000599351     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00457-6     Document Type: Article

References (21)

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12. M. B. Sassaman, G. K. S. Prakash, G. A. Olah, J. Org. Chem. 1990, 55, 2016; J. C. Mullis, W. P. Weber, J. Org. Chem. 1982, 47, 2873; K. Imi, N. Yanagihara, K. Utimoto, J. Org. Chem. 1987, 52, 1013; W. Nagata, M. Yoshioka, T. Okumura, J. Chem. Soc (C) 1970, 2365.
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15. 7 the thus obtained products are pure enough to be used after the usual workup without additional purification.
16. Compounds 9B, 10A and 10B could be isolated diastereomerically pure by flash chromatography, but in small quantities, just to be individually characterized.
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18. See J. C. Carretero, J. L. García Ruano, J. H. Rodríguez, Tetrahedron. 1985, 41, 2433; M. C. Carreño, J. C. Carretero, J. L. García Ruano, J. H. Rodríguez Tetrahedron. 1990, 46, 5649 and references therein.
19. Different experimental evidence supporting this mechanistic proposal implying inversion at the sulfur configuration will be published in due course.
20. The use of water gave similar results but the reactions were not so clean as with methanol.
21. Y. D. Vankar, C. Trinadha Rao, Tetrahedron Lett. 1985, 26, 2717.