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Volumn 47, Issue 10, 2006, Pages 1607-1611

SmI2-Promoted novel tandem elimination and coupling reactions of aliphatic imides with carbonyl compounds: Application to the synthesis of dl-isoretronecanol

Author keywords

Imide; Isoretronecanol; Pyrrolizidine alkaloid; Reductive coupling; SmI2

Indexed keywords

HEMPA; ISORETRONECANOL; PYRROLIZIDINE ALKALOID; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

EID: 31944434226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.126     Document Type: Article
Times cited : (23)

References (58)
  • 43
    • 31944432928 scopus 로고    scopus 로고
    • note
    • 9e
  • 44
    • 0009093553 scopus 로고
    • We could not prepare the hydroxyalkylated imide 2 from direct coupling reaction of N-benzylsuccinimide with butanal in the presence of base (cf. L. Lozzi, A. Ricci, and M. Taddei J. Org. Chem. 49 1984 3408 )
    • (1984) J. Org. Chem. , vol.49 , pp. 3408
    • Lozzi, L.1    Ricci, A.2    Taddei, M.3
  • 48
    • 31944448849 scopus 로고    scopus 로고
    • note
    • 16 as shown below: The other compounds were also estimated to have the same stereochemistry based on the similarity of its spectral data to those of threo-2 (R = Bn).
  • 52
    • 31944443187 scopus 로고    scopus 로고
    • note
    • 2 and an aldehyde-alkyl group. In addition, the alkyl function would also prefer to be equatorial resulting in an increase of the threo-selectivity. Additional studies on the precise mechanistic origin of these reactions are in progress.
  • 57
    • 31944439841 scopus 로고    scopus 로고
    • note
    • 18


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.