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Volumn 130, Issue 3, 2008, Pages 875-886

Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS; STEREOCHEMISTRY;

EID: 38349089956     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074907+     Document Type: Article
Times cited : (155)

References (67)
  • 1
    • 38349095371 scopus 로고    scopus 로고
    • Enantioselective syn- or anti-selective Mannich-type reactions that use silyl enolates or glycine imines as nucleophiles: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 4584.
    • Enantioselective syn- or anti-selective Mannich-type reactions that use silyl enolates or glycine imines as nucleophiles: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 4584.
  • 14
    • 0037462104 scopus 로고    scopus 로고
    • Enantioselective syn- or anti-selective Mannich-type reactions of hydroxyketones, β-ketoesters, a trichloromethyl ketone, or an imide that use other than enamine catalysis: (a) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
    • Enantioselective syn- or anti-selective Mannich-type reactions of hydroxyketones, β-ketoesters, a trichloromethyl ketone, or an imide that use other than enamine catalysis: (a) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
  • 28
    • 0037028924 scopus 로고    scopus 로고
    • Enamine-based enantioselective syn-selective Mannich or Mannich-type reactions that use aldehydes or ketones as nucleophiles: (a) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
    • Enamine-based enantioselective syn-selective Mannich or Mannich-type reactions that use aldehydes or ketones as nucleophiles: (a) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
  • 59
    • 38349191108 scopus 로고    scopus 로고
    • Determination of the absolute stereochemistry of 15 generated by the 1-catalyzed reaction has been reported in our communication (ref 4a).
    • Determination of the absolute stereochemistry of 15 generated by the 1-catalyzed reaction has been reported in our communication (ref 4a).
  • 60
    • 38349115114 scopus 로고    scopus 로고
    • To obtain the Mannich products generated from the reactions of aldehyde nucleophiles in an excellent dr, quick and careful workup and purification procedures were required. For example, the dr values of the products slightly (up to 4% variation) changed during silica gel flash column chromatography. Diastereomers of 15 were inseparable by typical silica gel flash column chromatography see Supporting Information
    • To obtain the Mannich products generated from the reactions of aldehyde nucleophiles in an excellent dr, quick and careful workup and purification procedures were required. For example, the dr values of the products slightly (up to 4% variation) changed during silica gel flash column chromatography. Diastereomers of 15 were inseparable by typical silica gel flash column chromatography (see Supporting Information).
  • 62
    • 38349146784 scopus 로고    scopus 로고
    • Determination of the absolute stereochemistry of 16 generated by the 4-catalyzed reaction has been reported in our communication (ref 4b).
    • Determination of the absolute stereochemistry of 16 generated by the 4-catalyzed reaction has been reported in our communication (ref 4b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.