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Volumn , Issue 5, 2001, Pages 788-804

Novel DBU-MeOH-promoted one-pot stereoselective γ-functionalization of 1,3-dicarbonyls: An easy access to γ-arylidene, γ-alkylidene and γ-allylidene α-ketoesters and -amides

Author keywords

Aldol reaction; Alkylidene (or arylidene) cycloalkanones; ketoamides; ketoesters; functionalization

Indexed keywords

ALDEHYDES; DEHYDRATION; KETONES;

EID: 0035036042     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-12762     Document Type: Article
Times cited : (16)

References (102)
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    • Computer-assisted structural search on REACS or Beilsteindatabases gave no answer. Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Chap 1.1
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    • It has been shown that formaldehyde and other substituted aldehydes reacted selectively at the α-position of cyclic and acyclic 1,3-dicarbonyls to give, after a deacylative condensation, α,β-unsaturated compounds
    • (1977) J. Org. Chem. , vol.42 , pp. 1180
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    • a
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    • We have also shown that treating 1d with 1 equiv DBU in refluxing MeOH for 48 h or stirring at r.t. for 3 d gave the open chain ketoamide 11 (Figure 2)
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    • While 1c was totally unreactive, 1a gave methyl adipate resulting from a retro-Dieckmann ring cleavage, see ref. 33
  • 88
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    • note
  • 94
    • 0003791302 scopus 로고
    • Plenum Press, 3 An alternative mechanism involving the formation of the corresponding dianion which is known to react selectively at the γ-position with various electrophiles, 7,8,11,12 cannot be ruled out totally although it can hardly be accommodated with the protic medium and with the fact that a substoichiometric amount of DBU is sufficient for the transformation to occur (vide supra)
    • (1977) Advanced Organic Chemistry, Part B
    • Carey, F.A.1    Sundberg, R.J.2
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    • note


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.