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Volumn 49, Issue 31, 2008, Pages 4661-4665

Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLETHANOL; 3,5 DIMETHYLPYRIDINE; ARYLPROPIONIC ACID DERIVATIVE; BUTYRIC ACID; CARBOXYLIC ACID; DICYCLOHEXYLCARBODIIMIDE;

EID: 45049086966     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.036     Document Type: Article
Times cited : (7)

References (47)
  • 1
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    • For representative reviews, see:
    • For representative reviews, see:. Fu G. Acc. Chem. Res. 33 (2000) 412-420
    • (2000) Acc. Chem. Res. , vol.33 , pp. 412-420
    • Fu, G.1
  • 6
    • 66949131841 scopus 로고    scopus 로고
    • Clayden J.C. (Ed), Georg Thieme KG, Stuttgart
    • Eames J. In: Clayden J.C. (Ed). Synthesis by Resolution and Inversion Methods. Science of Synthesis Vol. 36 (2007), Georg Thieme KG, Stuttgart 341-421
    • (2007) Science of Synthesis , vol.36 , pp. 341-421
    • Eames, J.1
  • 7
    • 0033921576 scopus 로고    scopus 로고
    • For representative reviews, see:
    • For representative reviews, see:. Fu G. Acc. Chem. Res. 33 (2000) 412-420
    • (2000) Acc. Chem. Res. , vol.33 , pp. 412-420
    • Fu, G.1
  • 26
    • 0034599013 scopus 로고    scopus 로고
    • For parallel kinetic resolution reviews, see:
    • For parallel kinetic resolution reviews, see:. Eames J. Angew. Chem., Int. Ed. 39 (2000) 885-888
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 885-888
    • Eames, J.1
  • 31
    • 24344493479 scopus 로고    scopus 로고
    • For a comprehensive review of quasi-enantiomers, see:
    • For a comprehensive review of quasi-enantiomers, see:. Zhang Q., and Curran D.P. Chem. Eur. J. 11 (2005) 4866-4880
    • (2005) Chem. Eur. J. , vol.11 , pp. 4866-4880
    • Zhang, Q.1    Curran, D.P.2
  • 37
    • 45049088260 scopus 로고    scopus 로고
    • note
    • We assume that the chirality present in DCC plays no stereochemical role in these reactions.
  • 38
    • 45049088149 scopus 로고    scopus 로고
    • note
    • Using a sub-stoichiometric amount of 3,5-lutidine 18 (0.2 equiv) gave after 12 h the corresponding esters (rac)-anti- and (rac)-syn-16 in a combined 57% yield with a diastereoisomeric ratio of 82:18.
  • 39
    • 45049086355 scopus 로고    scopus 로고
    • note
    • Replacing 3,5-lutidine with 4-dimethylaminopyridine (DMAP) gave the corresponding ester (rac)-(anti)-16 in 69% yield with lower diastereocontrol [54% de (ratio 77:23 anti-:syn-)].
  • 40
    • 45049084019 scopus 로고    scopus 로고
    • note
    • 3).
  • 41
    • 45049086299 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy by derivatisation with (R)-Mosher's acid (2-methoxy-2-phenyl-2-trifluoroacetic acid) using a DCC/DMAP (0.2 equiv) coupling procedure.
  • 42
    • 45049083984 scopus 로고    scopus 로고
    • note
    • 25 +2.51 for (S,S)-anti-33:(S,R)-syn-33 in the ratio 82:18}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.