Efficient synthesis of β-hydroxy-α-amino acid derivatives via direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes

Chen X.; Zhu Y.; Qiao Z.; Xie M.; Lin L.; Liu X.; Feng X.

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Efficient synthesis of β-hydroxy-α-amino acid derivatives via direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes

机译：通过α-异硫氰酸根合酰亚胺与醛的直接催化不对称醛醇缩合反应可高效合成β-羟基-α-氨基酸衍生物

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An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98%) with excellent diastereo-(up to >99:1 d.r.) and enantioselectivities (up to >99% ee). A variety of aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol% l-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

机译：已开发出一种容易获得且有效的手性N，N'-二氧化镍（II）络合物催化剂，用于α-异硫氰酸根酰亚胺与醛的直接催化不对称醛醇缩合反应，该产物以中等产率生产高产率的产物（高达98％）具有出色的非对映异构体-（高达> 99：1 dr）和对映选择性（高达> 99％ee）。在存在2.5mol％的I-脯氨酸衍生的N，N′-二氧化物L5-镍（II）络合物的情况下，发现各种芳族，杂芳族，α，β-不饱和和脂族醛是合适的底物。该过程是耐空气的，并且容易用可用的试剂进行操作。基于实验研究，提出了一种可能的过渡态来解释反应性和不对称电感的起源。

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《Chemistry: A European journal》 |2010年第33期|共6页
作者
Chen X.; Zhu Y.; Qiao Z.; Xie M.; Lin L.; Liu X.; Feng X.;
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正文语种 eng
中图分类应用化学;
关键词
Aldol reaction; Amino acids; Asymmetric catalysis; Nickel; Nitrogen oxides;

机译：羟醛反应;氨基酸;不对称催化;镍;氮氧化物;

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专利

1. Efficient synthesis of β-hydroxy-α-amino acid derivatives via direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes [J] . Chen X., Zhu Y., Qiao Z., Chemistry: A European journal . 2010,第33期

机译：通过α-异硫氰酸根合酰亚胺与醛的直接催化不对称醛醇缩合反应可高效合成β-羟基-α-氨基酸衍生物
2. Efficient Synthesis of β-Hydroxy--Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of -Isothiocyanato Imide with Aldehydes [J] . Xiaohong Chen Yin Zhu Zhen Qiao Mingsheng Xie Lili Lin Dr. Xiaohua Liu Dr. Xiaoming Feng Prof. Dr. Chemistry - A European Journal . 2010,第33期

机译：-异硫氰酸基酰亚胺与醛的直接催化不对称醛醇缩合反应可高效合成β-羟基-氨基酸衍生物
3. Asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives via organocatalytic direct aldol reaction of α-isothiocyanato phosphonates with aldehydes [J] . Han W.-Y., Zhao J.-Q., Wu Z.-J., The Journal of Organic Chemistry . 2013,第20期

机译：通过α-异硫氰酸根合膦酸酯与醛的有机催化直接羟醛反应不对称合成β-羟基-α-氨基膦酸衍生物
4. Catalytic Asymmetric Synthesis of α-Amino Acid Derivatives: Approaches toward Green Sustainable Methodology for Preparation of Optically Active Amino Acids [C] . Yasuhiro Yamashita, Shu Kobayashi Asymmetric synthesis and application of α-amino acids . 2007

机译：催化不对称合成α-氨基酸衍生物：绿色可持续方法制备光学活性氨基酸的方法
5. I. A1,3- strain enabled retention of chirality during Bis-cyclization of β-ketoamides: Asymmetric synthesis and bioactivity of salinosporamide a and derivatives II. Optimization of an Organic syntheses procedure: asymmetric nucleophile-catalyzed aldol-lactonization with aldehyde acids [D] . Nguyen, Henry 2010

机译：I. A1,3-菌株能够在β-酮基酰胺的双环化过程中保留手性：salinosporamide a和衍生物II的不对称合成和生物活性。有机合成程序的优化：醛酸不对称亲核催化醛醇内酯化
6. Catalytic asymmetric direct aldol reaction of α-alkyl azlactones and aliphatic aldehydes [O] . Yang Zheng, Li Deng 2015

机译：α-烷基氮杂内酯与脂肪醛的催化不对称直接羟醛反应
7. Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes: An Efficient Approach to the Asymmetric Synthesis of anti-b-Hydroxy-a-Amino Acid Derivatives [O] . -1

机译：甘氨酸衍生的硅与醛烯醇衍生硅和非对映选择性的醛醇反应：一种有效的抗B-羟基-α-氨基酸衍生物合成的方法

Efficient synthesis of β-hydroxy-α-amino acid derivatives via direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes

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