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Volumn 7, Issue 19, 2001, Pages 4266-4271

Sequential elimination-reduction reactions promoted by samarium diiodide: Synthesis of 2,3-dideuterioesters or -amides

Author keywords

Deuterium; Elimination; Reduction; Samarium; Sequential reactions

Indexed keywords

ESTERS; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 0035477904     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011001)7:19<4266::AID-CHEM4266>3.0.CO;2-8     Document Type: Article
Times cited : (37)

References (32)
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    • For a review of the use of deuterium in studying the mechanism of heterogeneous organic catalysis, see: B. S. Gudkov, Russ. Chem. Rev. 1986, 55, 259-270.
    • (1986) Russ. Chem. Rev. , vol.55 , pp. 259-270
    • Gudkov, B.S.1
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    • Oxford University Press, Oxford
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    • (1986) Secondary Metabolism , pp. 23
    • Mann, J.1
  • 23
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    • note
    • Difficulties associated with the conjugated reduction of compounds bearing a cyclohexyl substituent have been documented: see ref. [10].
  • 24
    • 0003259593 scopus 로고    scopus 로고
    • note
    • + peaks of the corresponding non-deuterated compounds are either absent or very weak, indicating that these species are present to an extent of <1%.
  • 25
    • 33847573358 scopus 로고
    • (Eds.: L. A. Paquette), Wiley, Chichester
    • G. A. Molander, in Organic Reactions, Vol. 46 (Eds.: L. A. Paquette), Wiley, Chichester, 1994, p. 243.
    • (1994) Organic Reactions , vol.46 , pp. 243
    • Molander, G.A.1
  • 26
    • 0003124720 scopus 로고    scopus 로고
    • note
    • The saturated amide was not obtained from 2,3-dimethyl-4-phenyl-but-2-enamide.
  • 27
    • 0003256341 scopus 로고    scopus 로고
    • note
    • The metalation of compounds 2 with Zn affords an enolate, which undergoes a β-elimination reaction giving the corresponding α,β-unsaturated ester (see ref. [3].
  • 28
    • 0003256343 scopus 로고    scopus 로고
    • note
    • 2O gave ethyl 2-deuterio-3-hydroxybutanoate in very low yield.
  • 32
    • 0003128646 scopus 로고    scopus 로고
    • note
    • For the preparation of 2-chloro-3-hydroxyamides 1i-m, see ref. [4].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.