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Volumn 71, Issue 3, 2006, Pages 947-953

E- or Z-selective Knoevenagel condensation of acetoacetic derivatives: Effect of acylated substituent, that is, TEMPO and amines, as an auxiliary, and new accesses to trisubstituted E- and Z-2-alkenals and furans

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; CARBOXYLIC ACIDS; DERIVATIVES; ELECTRONS; SOLVENTS; THERMOSETS;

EID: 32144457342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051952w     Document Type: Article
Times cited : (34)

References (42)
  • 1
    • 0000248247 scopus 로고
    • Reviews: (a) Jones, G. Org. React. 1967, 15, 204.
    • (1967) Org. React. , vol.15 , pp. 204
    • Jones, G.1
  • 5
    • 84985278838 scopus 로고
    • (c) Tietze, L. F.; Beifuss, U. Liebigs Ann. Chem. 1988, 321-329. Recently, Ti-enolate of acetoacetate was shown to be useful for E-selectivity in some extent:
    • (1988) Liebigs Ann. Chem. , pp. 321-329
    • Tietze, L.F.1    Beifuss, U.2
  • 9
    • 20444380025 scopus 로고    scopus 로고
    • Z-isomers from acetoacetate derivatives were used in natural product syntheses: (a) Hong, R.; Chen, Y.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 3478-3481.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3478-3481
    • Hong, R.1    Chen, Y.2    Deng, L.3
  • 27
    • 32144442876 scopus 로고    scopus 로고
    • note
    • E- and Z-geometry of 3 was further confirmed by NOE experiments (Supporting Information).
  • 29
    • 32144448885 scopus 로고    scopus 로고
    • note
    • According to resonance structure ii, the oxa-2-cyclohexenyl substituent of 2c is considered to be of electron-withdrawing nature.
  • 30
    • 0004293179 scopus 로고    scopus 로고
    • Oxford University Press: Oxford, U.K.; Chapter 4
    • (a) Kirby, A. J. Stereoelectronic Effect; Oxford University Press: Oxford, U.K., 1996; Chapter 4.
    • (1996) Stereoelectronic Effect
    • Kirby, A.J.1
  • 32
    • 32144450620 scopus 로고    scopus 로고
    • note
    • 13C NMR absorption due to an acyl CO usually appears at higher field than that of E-isomers. for example, (Z)-3b, 202.4 ppm versus (E)-3b, 195.4 ppm.
  • 33
    • 32144445939 scopus 로고    scopus 로고
    • note
    • -1.
  • 34
    • 32144454187 scopus 로고    scopus 로고
    • note
    • The calculation was probed by using PM3 semiempirical energy minimizations (MOPAC2002 in CAChe Worksystem Pro 5.04).
  • 35
    • 32144436731 scopus 로고    scopus 로고
    • note
    • Formation of a small amount of conjugated amides iii as a byproduct was accompanied. In contrast to efficient condensations with aromatic aldehydes, the reaction of trans-cinnamaldehyde (2e) with 15 under the same conditions resulted in a low yield of the desired Z-adduct.
  • 39
    • 13744249187 scopus 로고    scopus 로고
    • and references therein
    • (b) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850-852 and references therein.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 850-852
    • Brown, R.C.D.1
  • 40
    • 0041837463 scopus 로고    scopus 로고
    • Syntheses of natural products bearing a trisubstituted furan-3-carboxyl structure: (a) Toro, A.; Deslongchamps, P. J. Org. Chem. 2003, 68, 6847-6852.
    • (2003) J. Org. Chem. , vol.68 , pp. 6847-6852
    • Toro, A.1    Deslongchamps, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.