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Volumn 71, Issue 12, 2006, Pages 4667-4670

Intramolecular 5-endo-trig aminomercuration of β-hydroxy-γ- alkenylamines: Efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues

Author keywords

[No Author keywords available]

Indexed keywords

AMINOMERCURATION; CASTANOSPERMINE; GLYCOSIDASE INHIBITORY ACTIVITIES;

EID: 33744938666     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0601617     Document Type: Article
Times cited : (65)

References (78)
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    • Brossi, A., Ed.; Academic Press: New York, Chapter 3
    • Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3.
    • (1986) The Alkaloids , vol.28
    • Howard, A.S.1    Michael, J.P.2
  • 56
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    • and references therein
    • (b) Cronin, L.; Murphy, P. V. Org. Lett. 2005, 7, 2691-2693 and references therein.
    • (2005) Org. Lett. , vol.7 , pp. 2691-2693
    • Cronin, L.1    Murphy, P.V.2
  • 65
    • 0035056125 scopus 로고    scopus 로고
    • These results are consistent with our earlier studies on the 1,3-addition of methyl- and allyl-magnesium bromide, as well as silyl ketene acetal of ethyl acetate to nitrone 2, in the presence of TMSOTf (1 equiv) at -78 °C in THF, which afforded a good diastereoselectivity in the favor of the D-gluco isomer (∼de 75%), see: (a) Saha, N. N.; Desai, V. N.; Dhavale, D. D. Tetrahedron 2001, 57, 39-46.
    • (2001) Tetrahedron , vol.57 , pp. 39-46
    • Saha, N.N.1    Desai, V.N.2    Dhavale, D.D.3
  • 70
    • 0036078638 scopus 로고    scopus 로고
    • and references therein
    • For reviews on the 1,3-addition of organometallic reagents to nitrones, see: (c) Lombardo, M.; Trombini, C. Curr. Org. Chem. 2002, 6, 695-713 and references therein.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 695-713
    • Lombardo, M.1    Trombini, C.2
  • 71
    • 84926285060 scopus 로고
    • Jackman, L. M., Sternhell, S., Eds.; Pergamon: Elmsford, NY
    • 13C NMR spectra of compounds 5a,b and 6a,b, in which a N-Cbz group is present, showed doubling of signals. This was due to isomerization by restricted rotation around C=N, see: Applications of NMR spectroscopy in organic chemistry; Jackman, L. M., Sternhell, S., Eds.; Pergamon: Elmsford, NY, 1978; p 361.
    • (1978) Applications of NMR Spectroscopy in Organic Chemistry , pp. 361
  • 74
    • 0344447095 scopus 로고    scopus 로고
    • Our results were found to be identical with that reported by J. Jurczak and co-workers in which the addition of vinylmagnesium bromide to -N(Bn)Cbz diprotected L-alaninal afforded syn/anti products in the ratio 23:77; see: (a) Gryko, D.; Urbanczyk-Lipkowska, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 4059-4067.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 4059-4067
    • Gryko, D.1    Urbanczyk-Lipkowska, Z.2    Jurczak, J.3
  • 75
  • 76
    • 33744920405 scopus 로고    scopus 로고
    • note
    • 2O at -50 °C afforded a 1:1 mixture of the anti/syn products in low yield. Performing the reaction at 0 °C also led to the same ratio, with a low combined yield (55%).
  • 77
    • 33744937164 scopus 로고    scopus 로고
    • note
    • The reaction at 0 °C also afforded a single diastereomer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.