Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases

Tiffner Maximilian; Novacek Johanna; Busillo Alfonso; Gratzer Katharina; Massa Antonio; Waser Mario

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Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases

机译：甘氨酸梭碱基碱对不对称反应的手性尿素 - 季铵盐杂交催化剂的设计

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Bifunctional chiral urea-containing quaternary ammonium salts can be straightforwardly synthesised in good yield and with high structural diversity via a scalable and operationally simple highly telescoped sequence starting from trans-1,2-cyclohexanediamine. These novel hybrid catalysts were systematically investigated for their potential to control glycine Schiff bases in asymmetric addition reactions. It was found that Michael addition reactions and the herein presented aldol-initiated cascade reaction can be carried out to provide enantiomeric ratios up to 95 : 5 and good yields under mild conditions at room temperature.

机译：含双功能性手性尿素的季铵盐可以通过从Trans-1,2-环己二胺开始的可伸缩和操作简单的高度伸缩序列，以良好的产量和高结构多样性，可以直接合成。系统地研究了这些新型杂化催化剂，以使其在不对称的添加反应中控制甘氨酸席夫碱的潜力。发现迈克尔添加反应和本文呈现的醛醇引发的级联反应可以进行，以提供高达95：5的对映体比率，并在室温下在温和条件下的良好产率。

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《RSC Advances》 |2015年第96期|共9页
作者
Tiffner Maximilian; Novacek Johanna; Busillo Alfonso; Gratzer Katharina; Massa Antonio; Waser Mario;
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作者单位

Johannes Kepler Univ Linz Inst Organ Chem A-4040 Linz Austria;

Johannes Kepler Univ Linz Inst Organ Chem A-4040 Linz Austria;

Univ Salerno Dept Biol &

Chem I-84084 Fisciano Italy;

Johannes Kepler Univ Linz Inst Organ Chem A-4040 Linz Austria;

Univ Salerno Dept Biol &

Chem I-84084 Fisciano Italy;

Johannes Kepler Univ Linz Inst Organ Chem A-4040 Linz Austria;

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正文语种 eng
中图分类化学;
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1. Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases [J] . Tiffner Maximilian, Novacek Johanna, Busillo Alfonso, RSC Advances . 2015,第96期

机译：甘氨酸梭碱基碱对不对称反应的手性尿素 - 季铵盐杂交催化剂的设计
2. Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions [J] . Hong-Gang Cheng, Liang-Qiu Lu, Tao Wang, Chemical Communications . 2012,第45期

机译：手性亚砜-席夫碱杂化物的设计及其在铜催化不对称亨利反应中的应用
3. Chiral Octahedral Complexes of Cobalt(III) as "Organic Catalysts in Disguise" for the Asymmetric Addition of a Glycine Schiff Base Ester to Activated Olefins [J] . Victor I. Maleev, Michael North, Vladimir A. Larionov Advanced synthesis & catalysis . 2014,第8期

机译：钴（III）手性八面体配合物作为“伪装的有机催化剂”，用于将甘氨酸席夫碱酯不对称加成至活化烯烃
4. Development of Phase-Transfer-Catalyzed Asymmetric Strecker Reaction Based on the Molecular Design of Chiral Quaternary Ammonium Salts [C] . Takashi Ooi Asymmetric synthesis and application of α-amino acids . 2007

机译：基于手性季铵盐分子设计的相转移催化不对称Strecker反应研究
5. Asymmetric synthesis of stereochemically-defined and conformationally-constrained novel amino acids via direct alkylation of chiral nickel(II)-coordinated Schiff bases of glycine and alanine, and design and synthesis of selective peptide and non-peptide ligands for the delta-opioid receptor. [D] . Tang, Xue-jun. 2002

机译：通过手性镍（II）配位的甘氨酸和丙氨酸的席夫碱直接烷基化的立体化学定义和构象约束的新型氨基酸的不对称合成，以及δ阿片受体的选择性肽和非肽配体的设计和合成。
6. Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases [O] . Maximilian Tiffner, Johanna Novacek, Alfonso Busillo, -1

机译：甘氨酸席夫碱不对称反应的手性脲-季铵盐杂化催化剂的设计
7. Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases [O] . Tiffner, Maximilian, Novacek, Johanna, Busillo, Alfonso, 2015

机译：手性脲 - 季铵盐杂化催化剂用于甘氨酸席夫碱不对称反应的设计

Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases

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