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Volumn 4, Issue 17, 2002, Pages 2813-2816

A novel, stereoselective silyl-directed stevens [1,2]-shift of ammonium ylides

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; PYRROLIZIDINE ALKALOID; QUATERNARY AMMONIUM DERIVATIVE; QUINOLIZINE DERIVATIVE; SILANE DERIVATIVE;

EID: 0001635787     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025951r     Document Type: Article
Times cited : (61)

References (40)
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    • (b) Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913-974. Lepley, A. R.; Guimanini, A. G. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Interscience: New York, 1971; Vol. 3, pp 297-440.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 913-974
    • Markó, I.E.1
  • 3
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    • Thyagarajan, B. S., Ed.; Interscience: New York
    • (b) Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913-974. Lepley, A. R.; Guimanini, A. G. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Interscience: New York, 1971; Vol. 3, pp 297-440.
    • (1971) Mechanisms of Molecular Migrations , vol.3 , pp. 297-440
    • Lepley, A.R.1    Guimanini, A.G.2
  • 9
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    • For a prior discussion of the scope of this chemistry, see: West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115, 1177-1178.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1177-1178
    • West, F.G.1    Naidu, B.N.2
  • 10
    • 0034721683 scopus 로고    scopus 로고
    • Reviews: (a) El Nemr, A. Tetrahedron 2000, 56, 8579-8629.
    • (2000) Tetrahedron , vol.56 , pp. 8579-8629
    • El Nemr, A.1
  • 18
    • 0008681322 scopus 로고    scopus 로고
    • Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, UK
    • (a) Siehl, H.-U.; Muller, T. In Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, UK, 1998; Vol. 2, Parts 1-3, pp 595-701.
    • (1998) Chemistry of Organic Silicon Compounds , vol.2 , Issue.1-3 PARTS , pp. 595-701
    • Siehl, H.-U.1    Muller, T.2
  • 21
    • 0032856492 scopus 로고    scopus 로고
    • Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 4-646. For a recent report on the short lifetime of α-silyl radicals, see: Le Gall, E.; Hurvois, J.-P.; Sinbandhit, S. Eur. J. Org. Chem. 1999, 2645, 5-2653.
    • (1999) Eur. J. Org. Chem. , vol.2645 , pp. 5-2653
    • Le Gall, E.1    Hurvois, J.-P.2    Sinbandhit, S.3
  • 25
    • 84872269899 scopus 로고    scopus 로고
    • note
    • Strong support for this stereochemical assignment comes from the presence of a large 1,2-diaxial coupling between the adjacent bridgehead and silyl-substituted methines in the proton NMR spectrum.
  • 28
    • 84872274001 scopus 로고    scopus 로고
    • note
    • Retention was calculated as % ee of quinolizidines 4a (71%), 5a (63%), or 5b (77%) divided by % ee of 3a or 3b (both 85%).
  • 29
    • 84872263787 scopus 로고    scopus 로고
    • note
    • iPrOH/hex and a flow rate of 0.5 mL/min.
  • 30
    • 84872273152 scopus 로고    scopus 로고
    • note
    • Alkylation product 3b was found to decompose slowly under the conditions of its formation, requiring that the reaction be stopped prior to complete consumption of starting material. The same problem, though less severe, was encountered in the alkylation of 3a.
  • 31
    • 84872273480 scopus 로고    scopus 로고
    • note
    • 25NOSi: C, 71.03; H, 8.77; N, 4.87. Found: C. 71.0; H, 8.93; N, 4.52.
  • 32
    • 84872268719 scopus 로고    scopus 로고
    • note
    • Reduction with L-selectride or under Meerwein-Pondorff-Verley conditions also gave 6b exclusively, but in slightly lower yield.
  • 33
    • 84872270693 scopus 로고    scopus 로고
    • note
    • 2D NOESY NMR data clearly indicated the expected axial alcohol resulting from equatorial attack of the bulky hydride reagent.
  • 35
    • 84872272205 scopus 로고    scopus 로고
    • note
    • 3), indicating a small degradation in optical purity of 4b during the subsequent manipulations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.