Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α-Amino Acid or Amino Alcohol without Chiral Reagent

Thi Thoa Mai; Baby Viswambharan; Didier Gori; Régis Guillot; Jean-Valère Naubron; Cyrille Kouklovsky; Valérie Alezra

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Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α-Amino Acid or Amino Alcohol without Chiral Reagent

机译：叔芳族酰胺的冷冻手平性：没有手性试剂的氨基酸叔氨基酸或氨基醇的进入

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One of the fundamental and intriguing aspects of life is the homochirality of the essential molecules. In this field, the absolute asymmetric synthesis of a-amino acids is a major challenge. Herein, we report access, by chemical means, to tertiary a-amino acid derivatives in up to 96% ee without using any chiral reagent. In our strategy, the dynamic axial chirality of tertiary aromatic amides is frozen in a crystal and is responsible for the stereoselectivity of the subsequent steps. Furthermore, we could control the configuration of the final product by manually sorting and selecting the initial crystals. Based on vibrational circular dichroism studies, we could rationalize the observed stereoselectivity.

机译：生命的基本和有趣方面之一是必需分子的销售。在该领域中，A-氨基酸的绝对不对称合成是一个主要挑战。在此，我们通过化学方法向叔A-氨基酸衍生物报告高达96％EE的叔A氨基酸衍生物而不使用任何手性试剂。在我们的策略中，叔芳族酰胺的动态轴向手性被冷冻在晶体中，并负责后续步骤的立体选择性。此外，我们可以通过手动排序和选择初始晶体来控制最终产品的配置。基于振动圆形二色性研究，我们可以合理化观察到的立体选择性。

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来源
《Chemistry: A European journal》 |2017年第24期|共12页
作者
Thi Thoa Mai; Baby Viswambharan; Didier Gori; Régis Guillot; Jean-Valère Naubron; Cyrille Kouklovsky; Valérie Alezra;
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作者单位

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

Aix Marseille Université Centrale Marseille CNRS-Spectropole FR1739 13397 Marseille (France);

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

Univ. Paris-Sud Laboratoire de Méthodologie Synthèse et Molécules Thérapeutiques ICMMO UMR 8182 CNRS Université Paris-Saclay Bat 410 91405 Orsay (France);

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正文语种 eng
中图分类应用化学;
关键词
amino acids; amino alcohols; asymmetric amplification; asymmetric synthesis; chirality;

机译：氨基酸;氨基醇;不对称扩增;不对称合成;性儿;

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专利

1. Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α-Amino Acid or Amino Alcohol without Chiral Reagent [J] . Thi Thoa Mai, Baby Viswambharan, Didier Gori, Chemistry: A European journal . 2017,第24期

机译：叔芳族酰胺的冷冻手平性：没有手性试剂的氨基酸叔氨基酸或氨基醇的进入
2. Application of cyanuric chloride-based six new chiral derivatizing reagents having amino acids and amino acid amides as chiral auxiliaries for enantioresolution of proteinogenic amino acids by reversed-phase high-performance liquid chromatography [J] . Ravi Bhushan, Shuchi Dixit Amino Acids . 2012,第4期

机译：基于氰尿酰氯的六种新的氨基酸和氨基酸酰胺类手性衍生试剂作为手性助剂，用于反相高效液相色谱对映体拆分成蛋白氨基酸
3. Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient Method for the Enantioselective Synthesis of Quaternary α-Amino Acids [J] . Mathieu Branca, Sebastien Pena, Regis Guillot, Journal of the American Chemical Society . 2009,第30期

机译：芳香族手性手性的记忆：一种简单有效的方法，对映体合成季α-氨基酸。
4. ASYMMETRIC SYNTHESIS OF QUATERNARY AMINOACIDS USING THE MEMORY OF CHIRALITY OF TERTIARY AROMATIC AMIDES [C] . Cyrille Kouklovsky, Valerie Alezra, Mathieu Branca European Symposium on Organic Chemistry . 2009

机译：利用叔芳族酰胺的记忆的记忆不对称合成季氨基酰胺
5. Novel asymmetric indium-mediated Barbier-type addition reactions: The synthesis of allylborane reagents and chiral tertiary alcohols. [D] . Heddad, Terra Danielle. 2011

机译：新型不对称铟介导的Barbier型加成反应：烯丙基硼烷试剂和手性叔醇的合成。
6. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 12-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones [O] . Kangnan Li, Xinxin Shao, Luke Tseng, -1

机译：2-氮杂二烯用作制备手性胺的试剂：铜催化的酮与对映选择性还原偶联反应合成12-氨基叔醇
7. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones [O] . Kangnan Li, Xinxin Shao, Luke Tseng, 2018

机译：2-己二烯作为制备手性胺的试剂：用酮催化的致力化的对脑联系结合合成1,2-氨基叔醇

Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α-Amino Acid or Amino Alcohol without Chiral Reagent

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