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Volumn , Issue 23, 2000, Pages 3893-3901

On the stereoselectivity of γ-lactol substitutions with allyl- and propargylsilanes - Synthesis of disubstituted tetrahydrofuran derivatives

Author keywords

Carbocations; Felkin Anh model; Lewis acids; Silanes; Tetrahydrofuran

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; CARBENE; GAMMA LACTOL; PROPARGYLSILANE; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033676341     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E     Document Type: Article
Times cited : (78)

References (74)
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  • 20
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    • [8c] G. H. Posner, S. R. Haines, Tetrahedron Lett. 1985, 26, 1823-1826; see this ref. for reactions of activated or protected γ-lactols.
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  • 38
    • 0001897420 scopus 로고
    • D. S. Brown, P. Charreau, S. V. Ley, Synlett 1990, 749-750; see these refs. for related reactions of substituted 2-phenylsulfonyltetrahydrofurans.
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  • 39
    • 0001204097 scopus 로고
    • A. Schmitt, H.-U. Reißig, Synlett 1990, 40-42; see this ref. for preliminary communication of our results.
    • (1990) Synlett , pp. 40-42
    • Schmitt, A.1    Reißig, H.-U.2
  • 43
    • 0006909622 scopus 로고    scopus 로고
    • note
    • The corresponding cis-4,5-dimethyl-substituted γ-lactol could only be obtained as an enriched mixture with 5 as a minor component. However, its reaction with 8 in the presence of boron trifluoride is highly stereoselective, giving only the 2,4-trans-2,5-trans diastereomer (in admixture with the two isomers of 25). In this case, the two methyl groups cooperate, resulting in excellent diastereoselectivity.
  • 44
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    • manuscript in preparation
    • A. Schmitt, H.-U. Reißig, manuscript in preparation; for the preparation of (phenylselenenyl)tetrahydrofuran derivatives see this ref.
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  • 45
    • 0006989349 scopus 로고    scopus 로고
    • note
    • Unfortunately, the acetates derived from γ-lactols used in this study were rather unstable. Thus, we could not investigate stereoselectivity with these substrates.
  • 58
    • 33847537994 scopus 로고    scopus 로고
    • MM2 & P1, QCPE 395 +318 (P1) program packace PCMO-DEL, Serena Software
    • ]19] K. E. Gilbert, J. J. Gajewski, program MMX, version 89.000, MM2 & P1, QCPE 395 +318 (P1) program packace PCMO-DEL, Serena Software.
    • Program MMX, Version 89.000
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  • 61
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    • G. Rauhut, A. Schmitt, unpublished ab initio 6-31G* calculations, Technische Hochschule Darmstadt, 1991
    • G. Rauhut, A. Schmitt, unpublished ab initio 6-31G* calculations, Technische Hochschule Darmstadt, 1991.
  • 62
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    • The problem may be regarded as a Curtin-Hammett system with "feed in" mechanism, since the low activation barrier between the two conformers guarantees that their equilibrium is always established. For a discussion see: J. I. Seeman, Chem. Rev. 1983, 83, 83-134.
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    • Seeman, J.I.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.