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Volumn 61, Issue 15, 2005, Pages 3819-3833

Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions

Author keywords

Asymmetric synthesis; Evans' oxazolidinone; Polymer supported chiral auxiliary; Recovery and recycling; Solid phase asymmetric alkylation; Solid phase organic synthesis

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; LITHIUM DERIVATIVE; N (4 BENZYL 1,3 OXAZOLIDIN 2 ONE 3 CARBONYL)PIPERIDINE 4 CARBOXYLIC ACID; OXAZOLIDINONE DERIVATIVE; POLYMER; RESIN; UNCLASSIFIED DRUG;

EID: 15044359102     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.135     Document Type: Article
Times cited : (34)

References (63)
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    • 34 the dihedral angle between two methine hydrogens (H-4 and H-5) was 38.1°. This value and Karplus curve also supported the observed coupling constant. Furthermore, irradiation of H-5 in NMR gave a strong NOE for H-4. For a related example, P.H. Carter, J.R. LaPorte, P.A. Scherle, and C.P. Decicco Bioorg. Med. Chem. Lett. 13 2003 1237 1239
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  • 39
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    • note
    • A steric repulsion between benzyl and carboxamide moieties in cis-configuration was thought to provide the ideal environment for chirality induction, because the conformation of benzyl moiety at the 4-position is restricted around Re-face of the enolate intermediate to avoid the steric repulsion by the carboxamide moiety at the 5-position.
  • 40
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    • note
    • Crystallographic data (excluding structural factors) for the structure 15 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 259416. Copies of the data can be obtained, free of charge, on application to CDCC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223-336033 or e-mail: deposit@ccdc.cam.ac. uk ].
  • 41
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    • note
    • 3), suggesting that the reaction proceeded via a Z-configured lithium enolate intermediate.
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    • Enantiomeric excess of 26c was determined by HPLC analysis after conversion to the corresponding (S)-phenethylamide. E. Vedejs, and M. Gingras J. Am. Chem. Soc. 116 1994 579 588
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    • note
    • Energy minimization was performed by systematic conformation search on the MMFF94x force field using the Molecular Operating Environment modeling package (MOE 2004.03, Chemical Computing Group, Inc., Montreal, Canada), followed by MOPAC (PM3 program).
  • 45
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    • This effect may be similar to the shielding effect observed in 5,5-dimethyl-4-benzyloxazolidinone, so-called 'SuperQuats'. S.G. Davies, H.J. Sanganee, and P. Szolcsanyi Tetrahedron 55 1999 3337 3354
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    • T. Mukaiyama Angew. Chem., Int. Ed. Engl. 18 1979 707 721 Insufficient introduction (∼60%) of the N-3-phenylpropionyl group was observed in single coupling. Hence, double coupling was employed
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    • Mukaiyama, T.1
  • 49
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    • note
    • Other bases such as LiHMDS and KHMDS were less effective, and lower conversion was observed in the reaction below -20°C.
  • 50
    • 85030815113 scopus 로고    scopus 로고
    • note
    • 2 free condition. (b) Methanolysis of the recovered oxazolidinone resin 23 afforded the corresponding methyl ester 24 in 94% without any epimerization. Additionally there is no contamination of endo-cleavage byproduct as well as in the case of solution-phase model experiment.
  • 51
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    • 2, 10% Pd-C in EtOH resulted in not only reduction of olefin moiety, but also de-chlorination at the 2-position on the aromatic ring. 2,4-Dichlorobenzyl iodide was prepared by iodination of the corresponding alcohol with NaI/Amberlyst. M. Tajbakhsh, R. Hosseinzadeh, and Z. Lasemi Synlett 4 2004 635 638
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  • 52
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    • note
    • Absolute configuration of the products was determined in comparison to the specific rotations in literature; otherwise, corresponding authentic samples were prepared using (S)-4-benzyl-2-oxazolidinone. Yields were calculated from the original loading of Wang resin.
  • 53
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    • note
    • This type of side reaction is known in the standard Evans' chemistry and thought that the enolate intermediate partially decomposes via a ketene-pathway, see Ref. 15.
  • 55
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    • Carboxylic acid 26e is known as a key component of carboxypeptidase inhibitor, see: L.D. Byers, and R. Wolfenden Biochemistry 12 1973 2070 2078
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    • Byers, L.D.1    Wolfenden, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.