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Volumn 19, Issue 14, 2009, Pages 3955-3958

Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones

Author keywords

Aldol reaction; Chiral lactone; Jasmine lactone; Organocatalysis

Indexed keywords

CYCLOPENTANE DERIVATIVE; FORMALDEHYDE; LACTONE DERIVATIVE; PERFUME;

EID: 67649670046     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.012     Document Type: Article
Times cited : (30)

References (30)
  • 24
    • 67649674230 scopus 로고    scopus 로고
    • note
    • Typical procedure for Table 3, entry 1: To the solution of cyclopentanone (5, 463 μL, 5 mmol) in dichloromethane (1.0 mL) l-threonine (16, 36 mg, 0.3 mmol) was added. After stirring for 1 h at 25 °C, 37% aq formaldehyde solution (6, 75 μL, 1 mmol) was added. The reaction mixture was stirred for 48 h, then purified by flash silica gel column chromatography without further workup to provide aldol product (4a, 57 mg, 0.5 mmol, 50% yield).
  • 25
    • 67649667719 scopus 로고    scopus 로고
    • note
    • Reactions of cyclododecanone (12-membered) and/or cyclopentadecanone (15-membered) with aqueous formaldehyde in the presence of l-threonine resulted in no reaction.
  • 29
    • 44949251617 scopus 로고    scopus 로고
    • It has long been thought that a secondary enamine is better stabilized by hyperconjugation, whereas a primary amine gives the predominant imine form. However, recent advance on organocatalysis using primary amine, effective tautomerization of the iminium form to the enamine form proceeded, to construct carbon-carbon bond between the enamine and an acceptor progressed in a stereoselective fashion. See:
    • It has long been thought that a secondary enamine is better stabilized by hyperconjugation, whereas a primary amine gives the predominant imine form. However, recent advance on organocatalysis using primary amine, effective tautomerization of the iminium form to the enamine form proceeded, to construct carbon-carbon bond between the enamine and an acceptor progressed in a stereoselective fashion. See:. Xu L.-W., and Lu Y. Org. Biomol. Chem. 6 (2008) 2047
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 2047
    • Xu, L.-W.1    Lu, Y.2
  • 30
    • 0021062284 scopus 로고
    • The δ-lactone (S)-3 is a highly versatile intermediate, for example, in Corey's synthesis of leukotriene B. See:
    • The δ-lactone (S)-3 is a highly versatile intermediate, for example, in Corey's synthesis of leukotriene B. See:. Corey E.J., Pyne S.G., and Su W.G. Tetrahedron Lett. 24 (1983) 4883
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4883
    • Corey, E.J.1    Pyne, S.G.2    Su, W.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.