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Volumn , Issue 10, 2001, Pages 1845-1852

Intramolecular diels - Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring

Author keywords

Amides; Diels Alder reactions; Polycyclic aliphatic compounds; Pyrrolizidines; Radical reactions; Radicals

Indexed keywords

AMIDE; EXO N ACYL 3 AZA 10 OXATRICYCLO[5.2.1.0 1,5]DEC 8 ENE DERIVATIVE; HALOGEN; N ALLYL N (2 FURYLMETHYL)AMIDE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0035031690     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:10<1845::AID-EJOC1845>3.0.CO;2-I     Document Type: Article
Times cited : (27)

References (59)
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    • note
    • The same strategy was applied to the synthesis of 3-amino-1,3-pentadiene but this proved fruitless.
  • 50
    • 20644442342 scopus 로고    scopus 로고
    • note
    • Amide 6 was chosen because cyclization was expected to produce a small number of diastereomeric pyrrolizidines.
  • 51
    • 20644461361 scopus 로고    scopus 로고
    • note
    • The cis and trans stereochemical indicators refer to the relative position of the vinyl group with respect to the oxygen bridge.
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    • note
    • Energy calculations were performed using MM2.
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    • note
    • We cannot exclude the involvement of a selective retro Diels-Alder of 8b to rationalize the improvement in the diastereomers distribution, when 7 is converted into 8. However, the yield of 9 is expected to be much too little for the observed increment.
  • 57
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    • note
    • 6]DMSO.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.