Crystallisation-induced dynamic resolution of dipeptide-derived 5(4H)-oxazolones

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6575-6578

  Stock, H Thijs ^a   Turner, Nicholas J ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIN 5 ONE DERIVATIVE; DIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; EPIMER;

EID: 0029682693     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01403-7     Document Type: Article

References (33)

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13. This process has been called asymmetric transformation of the second kind or total spontaneous resolution. For reviews see: a) Eliel, E.L.; Wilen, S.H.; Mander, L.N. Stereochemistry of Organic Compounds; Wiley-Interscience, 1993, Chapter 7.
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21. These compounds are also referred to as azlactones or oxazolin-5(4H)-ones.
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29. 3).
30. 2 at 0°C. These conditions are known to give enantiomerically pure oxazolin-5(4H)-ones: Chen, F.M.F.; Kuroda, K.; Benoiton, N.L. Synthesis 1979, 230.
31. 2 (4 mL) for 5 min. After cooling to room temperature the precipitate was filtered off, giving 3.59 g (70%) of (S,R)-2b (d.e. 93%). The mother liquor contained (S,R)-2b (d.e. 13%) together with some minor impurities.
32. The extent of epimerisation of enantiomerically pure 5(4H)-oxazolones, when subjected to nucleophilic ring opening under basic conditions, depends on the ratio between the rate of substitution and the rate of epimerisation. It is known that hydrazine, although basic, reacts with 5(4H)-oxazolones to give ring opening without epimerisation (see ref. 13).
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