Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from phenylglycine

Tetrahedron Asymmetry

Volumn 19, Issue 13, 2008, Pages 1536-1548

  Chavda, Sameer ^a   Coulbeck, Elliot ^a   Dingjan, Marco ^a   Eames, Jason ^a   Flinn, Anthony ^b   Northen, Julian ^b  

^a UNIVERSITY OF HULL   (United Kingdom)

^b Onyx Scientific Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID; ESTER; HYDRATROPIC ACID; OXAZOLIDINE DERIVATIVE; PHENYLGLYCINE;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL;

EID: 47749088936     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.020     Document Type: Article

References (33)

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26. These levels of diastereocontrol correspond to an approximate selectivity factor, s, ranging from 11.5 (84% de) to 49 (96 de).
27. The addition of two (R)-enantiomeric lithiated oxazolidin-2-ones (1 equiv each) to pentafluorophenyl 2-(4-isobutylphenyl)propionate (S)-23 (1 equiv) in THF and stirring the resulting solution at -78 °C for 2 h, gave the corresponding (S,R)-syn-adducts which qualitatively revealed their relative rates of addition (assuming they have similar basicity). For oxazolidin-2-one combinations; (R)-1:(R)-14, (R)-2:(R)-14, (R)-1:(R)-2, (R)-1:(R)-13, (R)-14:(R)-13, and (R)-2:(R)-13, gave their corresponding (S,R)-syn-adducts in a relative proportion of 70:30, 70:30, 52:48, 100:0, 100:0 and 100:0, respectively.
28. The levels of diastereoselection were found to be dependent on the structural nature of the complementary oxazolidin-2-one. For example, for a sterically demanding oxazolidin-2-one, like (S)-14, the levels of diastereocontrol were higher for the parallel kinetic resolution of (rac)-8 using a complementary oxazolidin-2-one, such as either (R)-1, (R)-2 or (R)-13, than its corresponding mutual kinetic resolution [in the presence of (R)-14]. For additional information, see: Coulbeck, E.; Eames, J. Unpublished results.
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