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Volumn 3, Issue 8, 2001, Pages 1209-1212

Enantioselective synthesis of β-hydroxy acid derivatives via a one-pot aldol reaction-dynamic kinetic resolution

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; CARBON; ESTER; ETHER DERIVATIVE;

EID: 0035912310     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015682p     Document Type: Article
Times cited : (102)

References (46)
  • 1
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    • Review: (a) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
    • (1999) Chem. Rev. , vol.99 , pp. 1095-1120
    • Mahrwald, R.1
  • 11
    • 33845376099 scopus 로고
    • For an early report on direct catalytic asymmetric aldol reactions of aldehydes with isocyanoacetate giving high ee's, see: Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6405-6406
    • Ito, Y.1    Sawamura, M.2    Hayashi, T.3
  • 25
    • 0042364400 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 63063398 A2 19880319 Showa, 1988, 19 pp.
    • (c) Akita, H.; Matsukura, H.; Oishi, T. Jpn. Kokai Tokkyo Koho JP 63063398 A2 19880319 Showa, 1988, 19 pp.
    • Akita, H.1    Matsukura, H.2    Oishi, T.3
  • 26
    • 0041863460 scopus 로고    scopus 로고
    • (Chisso Corp., Japan). Eur. Pat. Appl. EP 451668 A2 19911016, 1991, 12 pp.
    • Kazutoshi, M.; Naoyuki, Y. (Chisso Corp., Japan). Eur. Pat. Appl. EP 451668 A2 19911016, 1991, 12 pp.
    • Kazutoshi, M.1    Naoyuki, Y.2
  • 36
    • 0041863458 scopus 로고    scopus 로고
    • note
    • TBME was chosen as solvent for the DKR due to the high enantiomeric ratio (E > 200) obtained with the PS-C lipase for our model substrate in this solvent.
  • 37
    • 0041863459 scopus 로고    scopus 로고
    • In the case of benzylic acetates, the elimination leads to a highly conjugated double bond
    • In the case of benzylic acetates, the elimination leads to a highly conjugated double bond.
  • 38
    • 0042865425 scopus 로고    scopus 로고
    • note
    • 2O).
  • 39
    • 0042865426 scopus 로고    scopus 로고
    • note
    • The kinetic resolution of compound 1a with the recovered enzyme gave the same E value. ee = enantiomeric excess of substrate (S) or product (P) and E = enantiomeric ratio (formula presented)
  • 41
    • 0000717383 scopus 로고
    • and references therein
    • (a) Boaz, N. W. J. Org. Chem. 1992, 57, 4289-4292 and references therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 4289-4292
    • Boaz, N.W.1
  • 44
    • 0028106548 scopus 로고
    • Kinetic resolution by acetate hydrolysis of methyl esters similar to compounds 2 having a methyl group in the α-position is known: Akita, H.; Chen, C. Y.; Nagumo, S. Tetrahedron: Asymmetry 1994, 5, 1207-1210.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1207-1210
    • Akita, H.1    Chen, C.Y.2    Nagumo, S.3
  • 45
    • 0031562040 scopus 로고    scopus 로고
    • For recent catalytic aldol reactions with preformed nonsubstituted silyl enol ethers giving high ee's, see: (a) Singer, R. A.; Carreira, E. M. Tetrahedron. Lett. 1997, 38, 927-930.
    • (1997) Tetrahedron. Lett. , vol.38 , pp. 927-930
    • Singer, R.A.1    Carreira, E.M.2
  • 46
    • 0012630382 scopus 로고    scopus 로고
    • Recent advances in asymmetric aldol addition reactions
    • Ojima, I. Ed.; Wiley-VCH: New York
    • (b) Carreira, E. M. Recent advances in asymmetric aldol addition reactions. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I. Ed.; Wiley-VCH: New York, 2000; pp 513-541.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 513-541
    • Carreira, E.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.