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Volumn 74, Issue 7-8, 2009, Pages 1069-1080

Addition of lithiated methoxyallene to aziridines - A novel access to enantiopure piperidine and β-amino acid derivatives

Author keywords

Amino ester; Alkynes; Allenes; Aziridines; Benzomorphan; Piperidones

Indexed keywords


EID: 72149084611     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc2009012     Document Type: Article
Times cited : (9)

References (86)
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    • 25. CCDC 720141 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk /conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
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    • This rearrangement may be caused by excess lithiated methoxyallene present or its presumed thermal decomposition product lithium methoxide. The process requires deprotonation at the terminal allene carbon and reprotonation in position 3 to generate the alkyne moiety. The overall driving force could be the subsequent deprotonation of the fairly acidic alkyne proton to afford the dianions of compounds 6. The fairly low yields indicate that considerable decomposition is occurring under these reaction conditions. For the formation of similar compounds by an alternative approach, see
    • This rearrangement may be caused by excess lithiated methoxyallene present or its presumed thermal decomposition product lithium methoxide. The process requires deprotonation at the terminal allene carbon and reprotonation in position 3 to generate the alkyne moiety. The overall driving force could be the subsequent deprotonation of the fairly acidic alkyne proton to afford the dianions of compounds 6. The fairly low yields indicate that considerable decomposition is occurring under these reaction conditions. For the formation of similar compounds by an alternative approach, see: Alouane N., Vrancken E., Mangeney P.: Synthesis 2007, 1261.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.