• 제목/요약/키워드: Chiral aldehyde

검색결과 15건 처리시간 0.025초

Asymmetric Cyanosilylation of Aldehydes by Chiral Ti-TADDOL Complex

  • Kim, Sung-Soo;Kwak, Ju-Myung;Rajagopal, Gurusamy
    • Bulletin of the Korean Chemical Society
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    • 제27권10호
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    • pp.1638-1640
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    • 2006
  • A variety of chiral cyanohydrins were readily prepared from aldehydes with TMSCN under the influence of chiral titanium complex formed in situ from $Ti(O^iPr)_4$/TADDOL(I) in the presence of $Ph_3PO$ as additive. The double activation method produces trimethylsilylethers in excellent yield (95%) with moderate enantiomeric excess.

Enantioselective Recognition of Amino Alcohols and Amino Acids by Chiral Binol-Based Aldehydes with Conjugated Rings at the Hydrogen Bonding Donor Sites

  • Kim, Ji-Young;Nandhakumar, Raju;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • 제32권4호
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    • pp.1263-1267
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    • 2011
  • Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

The Interaction of Chiral Amino Thiols with Organozinc Reagents and Aldehydes: A Mechanism of Amino Thiol-Catalyzed Addition of Organozinc Reagents to Aldehydes

  • 강자효;김진범;김지영;이덕환
    • Bulletin of the Korean Chemical Society
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    • 제19권4호
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    • pp.475-481
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    • 1998
  • Details of various equilibria involved in the reactions of oxaza- and thiazazincolidine catalysts, generated from either β-amino alcohol or β-amino thiol, with aldehyde were studied by colligative measurements. The results indicated that the coordination of diethylzinc prior to the coordination of aldehyde is essential for high enantioselectivity of the thiol catalyzed reaction. The probable origin of asymmetric nonlinearity is also presented.

Cinchona 알칼로이드를 키랄 리간드로 이용한 비대칭 Reformatsky 반응 (Enantioselective Reformatsky Reaction Using Cinchona Alkaloids as Chiral Ligands)

  • 박두한;최호진;이상기
    • 대한화학회지
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    • 제47권6호
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    • pp.597-600
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    • 2003
  • Cinchona 알칼로이드(1-4)들을 비대칭 Reformatsky 반응에 키랄 리간드로 사용하였다. 알데히드, 리간드, Reformatsky 시약의 적가 순서에 따라 반응의 수율이 달라지며, Reformatsky 시약과 알데히드, 리간드와의 비율도 수율에 크게 영향을 주었다.

Highly Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Novel Chiral tert-Amino Alcohols

  • Zhang, Cong-Hai;Yan, Sheng-Jiao;Pan, Sheng-Qiang;Huang, Rong;Lin, Jun
    • Bulletin of the Korean Chemical Society
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    • 제31권4호
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    • pp.869-873
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    • 2010
  • A series of novel chiral tert-amino alcohols 4a-h derived from enantiomerically pure phenylalanine were synthesized efficiently and used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc (diethylzinc-to-aldehyde addition). The use of 10 mol % of the amino alcohols led to the corresponding sec-alcohols with excellent enantioselectivities (up to 100% ee) and high yields.