메뉴 건너뛰기




Volumn 47, Issue 44, 2006, Pages 7715-7718

The first example of samarium diiodide-promoted intramolecular ketone-ester coupling of ketones tethering acyloxyalkyl side chains producing 2-hydroxy cyclic hemiacetals

Author keywords

Cyclic hemiacetals; Intramolecular ketone ester coupling; Samarium diiodide

Indexed keywords

ACETAL DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; SAMARIUM DIIODIDE;

EID: 33748958288     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.126     Document Type: Article
Times cited : (17)

References (31)
  • 3
    • 0346787791 scopus 로고    scopus 로고
    • and references cited
    • Kagan H.B. Tetrahedron 59 (2003) 10351-10372 and references cited
    • (2003) Tetrahedron , vol.59 , pp. 10351-10372
    • Kagan, H.B.1
  • 4
    • 0010077452 scopus 로고
    • Representative reviews:
    • Representative reviews:. Molander G.A. Chem. Rev. 92 (1992) 29-68
    • (1992) Chem. Rev. , vol.92 , pp. 29-68
    • Molander, G.A.1
  • 18
    • 0026691264 scopus 로고
    • The reactions of these types of substrates with Ti(0)-graphite:
    • The reactions of these types of substrates with Ti(0)-graphite:. Furstner A., and Jumbam D.N. Tetrahedron 48 (1992) 5991-6010
    • (1992) Tetrahedron , vol.48 , pp. 5991-6010
    • Furstner, A.1    Jumbam, D.N.2
  • 19
    • 33748957802 scopus 로고    scopus 로고
    • note
    • 13C NMR, and IR data.
  • 20
    • 33748966160 scopus 로고    scopus 로고
    • note
    • 3) δ 152.4, 141.2, 134.8, 130.4, 127.7, 125.4, 124.5, 115.5, 101.4, 75.0, 55.7, 43.3, 22.0, 17.6.
  • 21
    • 33748957080 scopus 로고    scopus 로고
    • note
    • Also, the cis-configuration of dihydroxy substituents of 2c was demonstrated by X-ray crystallography. The details will be reported in a full paper.
  • 22
    • 33748985876 scopus 로고    scopus 로고
    • note
    • 3) δ 201.5, 140.3, 134.5, 129.6, 129.2, 127.6, 126.9, 79.5, 68.8, 43.3, 37.1, 21.2, 17.2. In the cases of 1b-d, prolonged reactions did not significantly change the product distributions. For example, 2b-d were still major products, 55%, 58%, and 55%, respectively. And only small amounts of 5c (4%) and 5d (5%) were isolated.
  • 27
    • 33748968184 scopus 로고    scopus 로고
    • note
    • 5 an intramolecular ketone-ester coupling proceeded in the absence of t-BuOH. Upon addition of proton donors, a simple reduction of ketone carbonyl predominantly occurred and therefore alcohols were mainly obtained.
  • 29
    • 33748968888 scopus 로고    scopus 로고
    • note
    • The less reactivity of 10d compared to 10a could be rationalized in terms of the relative stability of the expected secondary carbocation 14d to tertiary carbocation 14a. On the other hand, it seems difficult to explain the effect of phenyl substituent of 10c on the reaction. One tentative explanation is that bulky phenyl substituent would somewhat interfere 1,2-carbon shift in 14c.
  • 31
    • 0023900629 scopus 로고
    • Some phosphates of furanose sugars possessing 2-hydroxy cyclic hemiacetal structures were reported as potential enzyme inhibitors:
    • Some phosphates of furanose sugars possessing 2-hydroxy cyclic hemiacetal structures were reported as potential enzyme inhibitors:. Maryanoff B.E., Reitz A.B., and Nortey S.O. Tetrahedron 44 (1988) 3093-3106
    • (1988) Tetrahedron , vol.44 , pp. 3093-3106
    • Maryanoff, B.E.1    Reitz, A.B.2    Nortey, S.O.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.