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Volumn , Issue 3, 2009, Pages 378-386

Synthesis and use of achiral oxazolidine-2-thiones in selective preparation of trans 2,5-disubstituted tetrahydrofurans

Author keywords

Diastereoselectivity; Furans; Glycosylation; Lactols; Natural products; Titanium

Indexed keywords


EID: 58649107138     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800907     Document Type: Article
Times cited : (18)

References (29)
  • 16
    • 58649098232 scopus 로고    scopus 로고
    • Conversion to the methyl esters during methanolysis did not erode the dr by retro-Michael-Michael equilibration because the observed ratios were in the range of 1:1 to 100:0 if equilibration occurred dr would be expected to be quite similar, Nevertheless, partial retro-Michael-Michael equilibration cannot definitely be ruled out as the relative rate of the methanolysis/retro-Michael reactions could also be dependent on the oxazolidine-2-thione. We thank one of the referees for pointing out this mechanistic issue
    • Conversion to the methyl esters during methanolysis did not erode the dr by retro-Michael-Michael equilibration because the observed ratios were in the range of 1:1 to 100:0 (if equilibration occurred dr would be expected to be quite similar). Nevertheless, partial retro-Michael-Michael equilibration cannot definitely be ruled out as the relative rate of the methanolysis/retro-Michael reactions could also be dependent on the oxazolidine-2-thione. We thank one of the referees for pointing out this mechanistic issue.
  • 17
    • 0000784039 scopus 로고
    • Phenyl groups may be smaller than a methyl group in some conditions, see
    • Phenyl groups may be smaller than a methyl group in some conditions, see: W. R. Roush, J. Org. Chem. 1991, 56, 4151.
    • (1991) J. Org. Chem , vol.56 , pp. 4151
    • Roush, W.R.1
  • 18
    • 0027135535 scopus 로고
    • See also the addition of 2-(trimethylsilyloxy)furan to lactol acetates
    • See also the addition of 2-(trimethylsilyloxy)furan to lactol acetates: B. Figadère, C. Chaboche, J.-F. Peyrat, A. Cavé, Tetrahedron Lett. 1993, 34, 8093-8096.
    • (1993) Tetrahedron Lett , vol.34 , pp. 8093-8096
    • Figadère, B.1    Chaboche, C.2    Peyrat, J.-F.3    Cavé, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.