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Volumn 13, Issue 2, 2011, Pages 216-219

A practical synthesis of trans -3-substituted proline derivatives through 1,4-addition

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DRUG DERIVATIVE; PROLINE;

EID: 78651484734     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102613z     Document Type: Article
Times cited : (38)

References (57)
  • 8
    • 78651513989 scopus 로고    scopus 로고
    • Latest example
    • Latest example: DeSolms, S. J.
    • Desolms, S.J.1
  • 9
    • 78651511971 scopus 로고    scopus 로고
    • U.S. Patent 5,872,135, 1999; CAN 130:196955
    • U.S. Patent 5,872,135, 1999; CAN 130:196955.
  • 11
    • 78651495257 scopus 로고    scopus 로고
    • Recent variants of this method exploit an organocatalytic key step
    • Recent variants of this method exploit an organocatalytic key step
  • 14
    • 78651511418 scopus 로고    scopus 로고
    • For other syntheses of compounds of type 2, see
    • For other syntheses of compounds of type 2, see
  • 20
    • 78651497505 scopus 로고    scopus 로고
    • For noncatalytic 1,4-additions to substituted dehydroprolines, see
    • For noncatalytic 1,4-additions to substituted dehydroprolines, see
  • 23
    • 78651512633 scopus 로고    scopus 로고
    • Reviews
    • Reviews
  • 27
    • 34147221694 scopus 로고    scopus 로고
    • For a recent contribution from this laboratory, see:; Angew. Chem., Int. Ed. 2008, 47, 7718-7721
    • Lopez, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179-188 For a recent contribution from this laboratory, see: Robert, T.; Velder, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2008, 47, 7718-7721
    • (2007) Acc. Chem. Res. , vol.40 , pp. 179-188
    • Lopez, F.1    Minnaard, A.J.2    Feringa, B.L.3    Robert, T.4    Velder, J.5    Schmalz, H.-G.6
  • 34
    • 78651512365 scopus 로고    scopus 로고
    • For the NCS-oxidation of amines to N -chloroamines, see
    • For the NCS-oxidation of amines to N -chloroamines, see
  • 37
    • 78651482993 scopus 로고    scopus 로고
    • 3 nor pyridine could be replaced by each other. Pyridine proved not to be basic enough to induce HCl elimination (7 to 8) while we assume pyridine to act as a catalyst in the acylation of 8
    • 3 nor pyridine could be replaced by each other. Pyridine proved not to be basic enough to induce HCl elimination (7 to 8) while we assume pyridine to act as a catalyst in the acylation of 8.
  • 38
    • 78651488051 scopus 로고    scopus 로고
    • With 1.5 equiv of Cbz-Cl/pyridine the yield of 3a dropped to 30%
    • With 1.5 equiv of Cbz-Cl/pyridine the yield of 3a dropped to 30%.
  • 41
    • 78651483274 scopus 로고    scopus 로고
    • 1H NMR of the purified sample
    • 1H NMR of the purified sample.
  • 43
    • 0000106921 scopus 로고
    • Not unexpected, the diastereomers could not be separated by column chromatography; see ref 6 and
    • Not unexpected, the diastereomers could not be separated by column chromatography; see ref 6 and Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710-1716
    • (1974) J. Org. Chem. , vol.39 , pp. 1710-1716
    • Sarges, R.1    Tretter, J.R.2
  • 44
    • 78651479309 scopus 로고    scopus 로고
    • 1H NMR (400 MHz). The nonconverted starting material (rac-10) was re-isolated as a mixture of trans and cis diastereomers
    • 1H NMR (400 MHz). The nonconverted starting material (rac-10) was re-isolated as a mixture of trans and cis diastereomers.
  • 46
    • 78651500902 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 51
    • 78651500124 scopus 로고    scopus 로고
    • 1H NMR. The assumed trans-configuration of both major isomers was confirmed after hydrolysis to 2a. The formation of minor amounts of cis -isomers cannot be excluded because of the complexity of the NMR spectra on the stage of 15
    • 1H NMR. The assumed trans-configuration of both major isomers was confirmed after hydrolysis to 2a. The formation of minor amounts of cis -isomers cannot be excluded because of the complexity of the NMR spectra on the stage of 15.
  • 52
    • 84985531889 scopus 로고
    • 3-mediated 1,4-addition of a vinyl-Cu reagent to 14 (according to) proceeded in 82% yield, however, with lower selectivity (dr = 3.2:1)
    • 3-mediated 1,4-addition of a vinyl-Cu reagent to 14 (according to Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959) proceeded in 82% yield, however, with lower selectivity (dr = 3.2:1)
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 947-959
    • Yamamoto, Y.1
  • 54
    • 78651506723 scopus 로고    scopus 로고
    • 1H NMR (integration of the H-2 signals at ca. 5.5 ppm)
    • 1H NMR (integration of the H-2 signals at ca. 5.5 ppm).


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