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Volumn 52, Issue 18, 2011, Pages 2330-2332

Microwave-promoted tandem reactions for the synthesis of bicyclic γ-lactams

Author keywords

Kharasch cyclisation; Microwave synthesis; Overman rearrangement; Ring closing metathesis; Tandem reactions

Indexed keywords

GAMMA LACTAM DERIVATIVE;

EID: 79953289593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.089     Document Type: Article
Times cited : (15)

References (27)
  • 20
    • 79953283333 scopus 로고    scopus 로고
    • All allylic alcohols used in this study were prepared as previously reported. See Ref. 7 for full details
    • All allylic alcohols used in this study were prepared as previously reported. See Ref. 7 for full details.
  • 22
    • 79953280506 scopus 로고    scopus 로고
    • During previous studies on the Kharasch cyclisation of cyclic allylic trichloroacetamides, we found that 4 Å molecular sieves act as an effective acid scavenger resulting in high yields of products. See Refs. 4b,7 for full details
    • During previous studies on the Kharasch cyclisation of cyclic allylic trichloroacetamides, we found that 4 molecular sieves act as an effective acid scavenger resulting in high yields of products. See Refs. 4b,7 for full details.
  • 23
    • 79953274866 scopus 로고    scopus 로고
    • Although racemic, the bicyclic γ-lactams formed from this tandem process are isolated as single diastereomers.
    • Although racemic, the bicyclic γ-lactams formed from this tandem process are isolated as single diastereomers.
  • 25
    • 79953278180 scopus 로고    scopus 로고
    • note
    • 3 (0.02 g) and a silicon carbide (SiC) bar. The vial was then sealed under Ar and the reaction mixture heated in a microwave reactor (Biotage initiator, 300 W) for the required time at 180 °C. Grubbs first-generation catalyst (10 mol %) was added and the mixture was heated at 60 °C until complete. The temperature was then raised to 180 °C and heating continued until the reaction was complete. Purification was carried out by flash column chromatography eluting with petroleum ether/EtOAc to afford the desired bicyclic γ-lactam.
  • 26
    • 79953277184 scopus 로고    scopus 로고
    • The use of Hoveyda-Grubbs 2nd generation catalyst for the RCM and Kharasch steps gave more consistent yields of bicyclic γ-lactam 8 than using Grubbs 1st generation catalyst
    • The use of Hoveyda-Grubbs 2nd generation catalyst for the RCM and Kharasch steps gave more consistent yields of bicyclic γ-lactam 8 than using Grubbs 1st generation catalyst.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.