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Volumn 56, Issue 32, 2000, Pages 5793-5800

Intermolecular and intramolecular reactions of resolved 2-alkoxytetrahydrofuran-3-yl and 2-alkoxytetrahydropyran-3-yl radicals

Author keywords

Diastereoselection; Radicals and radical reactions; Resolution; Selenoacetals

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; LACTIC ACID DERIVATIVE; MANDELIC ACID DERIVATIVE; PANTOLACTONE; RADICAL; SELENIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

EID: 0034604668     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00547-0     Document Type: Article
Times cited : (3)

References (35)
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  • 18
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    • We have assumed that all less polar THF and THP diastereomers derived from a particular α-hydroxyester enantiomer have related configurations at the acetal carbon, and all more polar diastereomers have the opposite configuration. Thus far this has proved to be the case. The less polar diastereomer i was converted to known tetrabenzoate ii; see Ref. 5. The structure of more polar diastereomer iii was established by X-ray crystallography (J. Fryling, unpublished results)
  • 19
    • 85037928452 scopus 로고    scopus 로고
    • Use of (S)-methyl mandelate as the chiral auxiliary gave products derived from intramolecular abstraction of the benzylic hydrogen
  • 20
    • 85037946269 scopus 로고    scopus 로고
    • Diastereomer ratios for product THP acetals having (S)-methyl lactate or (S)-methyl hexahydromandelate as the chiral auxiliary were approximately 1:1; see Ref 1
  • 25
    • 85037949145 scopus 로고    scopus 로고
    • Greater diastereoselectivity for the methyl acrylate trap is consistent with the literature; see Ref. 10
  • 26
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    • The predominance of 14a over 14b reflects kinetic control of this exchange reaction at short reaction times. Use of long reaction times resulted in equilibration to approximately a 1:1 mixture of 14a and 14b
  • 32
    • 85037943408 scopus 로고    scopus 로고
    • For compound 15, irradiation of proton H(a) increased the intensities of protons H(b) and H(c) by 3.3 and 1.2%, respectively. Irradiation of H(b) increased the intensities of protons H(a) and H(c) by 3.7 and 2.8%, respectively
  • 35
    • 85037931037 scopus 로고    scopus 로고
    • 2 containing 10 equiv. of allyl alcohol gave, in 88% yield, a chromatographically inseparable 10:1 mixture of the corresponding diastereomeric allyl pyranosides. Radical generation, cyclization, and trapping with acrylonitrile afforded a 5:1 mixture of acetals iv and v (see Ref. 1)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.