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Volumn 9, Issue 5, 2007, Pages 891-894

Conjugate addition of 2- and 4-pyridylcuprates: An expeditious asymmetric synthesis of natural (-)-evoninic acid

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; ETHER; EVONINIC ACID; PROPIONIC ACID DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33947146141     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070011y     Document Type: Article
Times cited : (41)

References (28)
  • 11
    • 4644252638 scopus 로고    scopus 로고
    • 2Zn: Peña, D.; López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1836 and references therein.
    • 2Zn: Peña, D.; López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1836 and references therein.
  • 12
    • 5644222576 scopus 로고    scopus 로고
    • ArMgX: López, F.; Hurutyunyun, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2004, 126, 12784 and references therein.
    • (b) ArMgX: López, F.; Hurutyunyun, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2004, 126, 12784 and references therein.
  • 15
    • 0000696943 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (c) Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4. p 169.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 169
    • Kozlowski, J.A.1
  • 23
    • 0000350730 scopus 로고    scopus 로고
    • The significant variation of the diastereoselectivity of this alkylation reaction as a function of the enolate counterion and solvent is noteworthy. Few similarly dependent alkylations and protonations have been reported: (a) Stork, G, Boeckman, R. K. J. Am. Chem. Soc. 1973, 95, 2016
    • The significant variation of the diastereoselectivity of this alkylation reaction as a function of the enolate counterion and solvent is noteworthy. Few similarly dependent alkylations and protonations have been reported: (a) Stork, G.; Boeckman, R. K. J. Am. Chem. Soc. 1973, 95, 2016.
  • 26
    • 33947117183 scopus 로고    scopus 로고
    • The following hydrolyses were screened: pig liver esterase (PLE), immobilized PLE, lipase P. cepacia, lipase P. fluorescens, Candida antactica lipase B (Novozym-435), and α-chymotrypsin.
    • The following hydrolyses were screened: pig liver esterase (PLE), immobilized PLE, lipase P. cepacia, lipase P. fluorescens, Candida antactica lipase B (Novozym-435), and α-chymotrypsin.
  • 27
    • 33947162739 scopus 로고    scopus 로고
    • 1H NMR spectrum with that of a 1:1 mixture of diastereoisomers obtained likewise from acid (±)-10s (see Supporting Information).
    • 1H NMR spectrum with that of a 1:1 mixture of diastereoisomers obtained likewise from acid (±)-10s (see Supporting Information).


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