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Volumn , Issue 17, 2006, Pages 3969-3976

Stereochemistry of the tetrabutylammonium cyanide-catalyzed cyanosylilation of cyclic α,β-epoxyketones - Dependence of the diastereoselectivity on the ring size

Author keywords

Ab initio calculations; Cyanohydrins; Diastereoselectivity; Epoxyketones; Tetrabutylammonium cyanide; Trimethylsilyl cyanide

Indexed keywords


EID: 33748577211     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600239     Document Type: Article
Times cited : (13)

References (52)
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    • For a recent review on the synthesis of racemic tertiary cyanohydrins, see: a) F-X. Chen, X. Feng, Synlett 2005, 892;
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    • In a recent review on the synthetic applications of α,β- epoxyketones, this transformation and these types of compounds have not been referenced or mentioned, see: a) C. Lauret, Tetrahedron: Asymmetry 2001, 12, 2359;
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    • 4-catalyzed addition of TMSCN to open-chain α,β-epoxyaldehydes has been described, see: b) J. Ipaktschi, A. Heydari, H. O. Kalinowski, Chem. Ber. 1994, 127, 905.
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    • note
    • No other epoxidation reagents were tried.
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    • note
    • See Supporting Information for full details.
  • 33
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    • note
    • Calculations of the relative stabilities of compounds 7-11 rule out the possibility of the thermodynamic equilibration of the syn and anti isomers, see Table 2.
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    • + cation through co-ordination to the carbonyl oxygen may also be considered. For a related report, see: J. M. Blackwell, D. J. Morrison, W. E. Piers, Tetrahedron 2002, 58, 8247. In any case, this supplementary catalytic role should not affect the stereochemical result.
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    • John Wiley & Sons, NY
    • For a discussion on the interplay of steric and electronic factors in the nucleophilic addition to carbonyl compounds, see: a) E. L. Eliel, S. H. Wilen in Stereochemistry of Organic Compounds, John Wiley & Sons, NY, 1994, pp. 875-887;
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.