• Title/Summary/Keyword: Chiral aldehyde

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Highly Diastereoselective Aldol-Type Reaction Using 3-Acetylthiazolidine-2-thione (3-아세틸티아졸리딘-2-티온을 이용한 입체선택적인 알돌-축합반응)

  • Tae Myeong Jeong;Ki Hun Park
    • Journal of the Korean Chemical Society
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    • v.33 no.4
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    • pp.426-430
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    • 1989
  • Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various ${\beta}$-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.

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Synthesis and Phytotoxic Activities of (8S, 9S, 11R)-(-)-Monocerin and (9S, 11R)-(+)-Fusarentin 4, 5-dimethyl ether ((8S, 9S, 11R)-(-)-Monocerin and (9S, 11R)-(+)-Fusarentin 4, 5-dimethyl ether의 합성과 생리활성)

  • Ko, Byoung-Seob
    • Applied Biological Chemistry
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    • v.37 no.5
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    • pp.402-408
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    • 1994
  • For the examination of the role of monocerin(1) on the biological activity, (8S, 9S, 11R)-(-)-monocerin(20) and (9S, 11R)-(+)-fusarentin 4, 5-dimethyl ether(19) were synthesized by a condensation of the benzylic anion of ethyl 2, 3, 4-trimethoxy-6-methylbenzoate(16) with modifyed (R)-ethyl 3-hydroxyhexanoate (9). In a key step, bioreduction with active dried baker's yeast in organic solvent system was employed to get a chiral aldehyde 12. Their phytotoxic activities were tested on rice seedlings and lettuce seeds.

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Facile Synthesis of the Uryl Pendant Binaphthol Aldehyde and Its Selective Fluorescent Recognition of Tryptophan

  • Tang, Lijun;Wei, Gongfan;Nandhakumar, Raju;Guo, Zhilong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.9
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    • pp.3367-3371
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    • 2011
  • An easy and convenient synthetic route to (S)-2-hydroxy-2'-(3-phenyluryl-benzyl)-1,1'-binaphthyl-3-carboxaldehyde (1), capable of recognizing tryptophan by fluorescence has been developed. The binol carboxaldehyde 1 exhibited a high selectivity to L-tryptophan over other examined L-${\alpha}$-amino acids such as alanine, phenylalanine, glutamine, arginine, lysine, serine, threonine, aspartat, valine, histidine and cysteine, with a fluorescence "turn-on" signal. In addition, 1 displayed chiral discrimination with good enantioselectivity toward L-tryptophan over D-tryptophan through different fluorescence enhancement factors.