• Title/Summary/Keyword: Aldol Reaction

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Acetate-Promoted Aldol-Type Reaction: Scope and Reactivity of Acetates and Aldehydes

  • Kim, Dong-Hyeon;Rahman, A. F. M. Motiur;Jeong, Byeong-Seon;Lee, Eung-Seok;Jahng, Yurng-dong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.4
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    • pp.797-802
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    • 2009
  • Potential of acetates and related compounds in glacial acetic acid as a catalyst for aldol-type condensation reactions was examined. Reactions of cycloalkanones or selected heteroaromatics with aldehydes in presence of 10 mol% of various acetates in acetic acid afforded ${\alpha},{\alpha}$'-bis(substituted-benzylidene)cycloalkanones and substituted-benzylidene-mackinazolinones, respectively, in good yields. Among the compounds tested, ammonium acetate is the best and effective especially towards the reactions of mackinazolinone and aliphatic aldehydes to afford 6-alkylidenemackinazolinones.

Design, Synthesis and Catalytic Property of L-Proline Derivatives as Organocatalysts for Direct Aldol Reaction

  • Wang, Lei;Tang, Ruiren;Yang, Hua
    • Journal of the Korean Chemical Society
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    • v.57 no.5
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    • pp.591-598
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    • 2013
  • A series of chiral prolinamide compounds with pyridine-2, 6-dicarboxylic acid moieties derived from L-proline have been designed and synthesized, their catalytic properties for direct asymmetric aldol reactions were also studied in this article. These catalysts gave the aldol product in high yield (87%) and high enantioselectivity, up to 85%, of the anti-structure at room temperature but gave disappointing results at a lower temperature or when additive was added. Conditions, including solvents, temperature and additives were screened for the reactions. Moreover, the influence of presence of water on yield and stereoselectivity was also discussed.

Introduction of a New Chiral Oxazolidin-2-one Derived from D-Mannitol and Its Applications as a Chiral Auxiliary

  • Kim, Si-Min;Jin, Hyun-Yong;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.23 no.5
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    • pp.749-757
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    • 2002
  • Chiral oxazolidin-2-one is easily prepared from D-mannitol and demonstrated to undergo highly diastereoselective alkylation reactions via lithium imide Z-enolates of its N-acyl derivatives to afford ${\alpha}-branched$ products. Evans syn and non-Evans sy n aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base. Also, this new auxiliary is employed in diastereoselective Staudinger-type ${\beta}-lactam$ syntheses. Using 2-chloro-1-methylpyridinium iodide as the dehydrating agent, the reaction of auxiliary tethered acetic acid with trans imines gave the desired ${\beta}-lactams$ with cis-selectivity.

A study of aldol condensation reaction product using a microreactor (마이크로 반응기를 적용한 알돌 축합반응 생성물 제조연구)

  • Kim Young-Jun;Lee Sang-Seo;Son Sung-Kwang;Song Kwang-Ho;Choe Jae-Hoon
    • Proceedings of the Korean Society of Precision Engineering Conference
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    • 2006.05a
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    • pp.543-544
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    • 2006
  • 3-methyl-2-cyclopentenone is a valuable reaction intermediate for various high value added products. 3-methyl-2-cyclopentenone is not only expensive but also difficult to produce. 3-methyl-2-cyclopentenone can be synthesized by base catalyzed intermolecular aldol condensation. In this work, we studied a simple and practical method for synthesizing 3-methyl-2-cyclopentenone. Experimental results showed the advantages of the continuous flow process using a microreactor with kenic mixers for the synthesis of 3-methyl-2-cyclopentenone.

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Aldol Condensation over Acid-Base Bifunctional Metal-Organic Framework Catalysts (산, 염기 이원기능 금속-유기 구조체 촉매를 이용한 알돌 축합반응)

  • Chung, Young-Min
    • Clean Technology
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    • v.20 no.2
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    • pp.116-122
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    • 2014
  • Various types of MOFs (metal-organic frameworks) were prepared via hydrothermal and post-grafting methods and applied as catalysts for the synthesis of jasminaldehyde, one of the representative perfume intermediates, by Aldol condensation of benzaldehyde with heptanal. Although both acid and base sites could catalyze the reaction, the catalytic performance was strongly dependent on the physical properties as well as the nature of functionalization on MOFs. While the use of sulfonated MOF catalysts led to decrease of jasminaldehyde selectivity regardless of MOFs used, the selectivity change was found to rely on the MOF types in the case of the amine-functionalization. Among the catalysts tested, MIL-101 shows the best catalytic performance, which may suggest that MIL-101 has suitable acid properties to promote the Aldol condensation and the large pore of MIL-101 is also advantageous to alleviate the diffusion problem of bulky products.