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Volumn 46, Issue 8, 2005, Pages 1287-1290

Straightforward synthesis of enantiopure 2-aminomethyl and 2-hydroxymethyl pyrrolidines with complete stereocontrol

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; LITHIUM; METHYL GROUP; OXIDE; OXYGEN; PYRROLIDINE DERIVATIVE;

EID: 13244299173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.119     Document Type: Article
Times cited : (52)

References (43)
  • 1
    • 0034607947 scopus 로고    scopus 로고
    • For recent reviews about natural occurrence, biological activity and therapeutic applications of natural hydroxylated pyrrolidines, see: N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645 1680
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1645-1680
    • Asano, N.1    Nash, R.J.2    Molyneux, R.J.3    Fleet, G.W.J.4
  • 8
    • 0036214511 scopus 로고    scopus 로고
    • For a review on recent advances in the synthesis of naturally occurring polyhydroxylated alkaloids, see: H. Yoda Curr. Org. Chem. 6 2002 223 243
    • (2002) Curr. Org. Chem. , vol.6 , pp. 223-243
    • Yoda, H.1
  • 16
    • 0142169426 scopus 로고    scopus 로고
    • For a recent review about synthesis of 2-hydroxymethyl pyrrolidines, see: E.-S.H. El-Ashry, and A. El Nemr Carbohydr. Res. 338 2003 2265 2290 and references cited therein
    • (2003) Carbohydr. Res. , vol.338 , pp. 2265-2290
    • El-Ashry, E.-S.H.1    El Nemr, A.2
  • 37
    • 13244285756 scopus 로고    scopus 로고
    • note
    • 2O) δ 36.6 (C-1′), 48.2 (C-5), 57.2 (C-2), 69.8 (C-4), 70.0 (C-3)
  • 40
    • 13244285835 scopus 로고    scopus 로고
    • note
    • Vinyl magnesium bromide addition to a related chiral cyclic nitrone followed by conversion of vinyl to hydroxymethyl through oxidative cleavage of CC double bond and reduction has been reported: Ref. 6f
  • 42
    • 13244280523 scopus 로고    scopus 로고
    • note
    • 13C NMR data of compounds 10 and 14 match those reported in the literature. The different assignment to protons at C-5 and C-1′, which are inverted, is based on bidimensional g-HMQC spectra, which unequivocally establish correlations of those protons with the connected carbon atoms


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.