Expanding the utility of Br?nsted base catalysis: Biomimetic enantioselective decarboxylative reactions

Pan Y.; Kee C.W.; Jiang Z.; Ma T.; Zhao Y.; Yang Y.; Xue H.; Tan C.-H.

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Expanding the utility of Br?nsted base catalysis: Biomimetic enantioselective decarboxylative reactions

机译：扩大布朗斯台德碱催化的效用：仿生对映选择性脱羧反应

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As a result of the low reactivity of simple esters, the use of them as nucleophiles in direct asymmetric transformations is a long-standing challenge in synthetic organic chemistry. Nature approaches this difficulty through a decarboxylative mechanism, which is used for polyketide synthesis. Inspired by nature, we report guanidine-catalyzed biomimetic decarboxylative C-C and C-N bond-formation reactions. These highly enantioselective decarboxylative Mannich and amination reactions utilized malonic acid half thioesters as simple ester surrogates. It is proposed that nucleophilic addition precedes decarboxylation in the mechanism, which has been investigated in detail through the identification of intermediates by using electrospray ionization (ESI) mass-spectrometric analysis and DFT calculations.

机译：由于简单酯的低反应性，在直接有机不对称转化中将它们用作亲核试剂是合成有机化学中的长期挑战。大自然通过用于聚酮化合物合成的脱羧机理解决了这一难题。受自然界的启发，我们报告了胍催化的仿生脱羧C-C和C-N键形成反应。这些高度对映选择性的脱羧曼尼希和胺化反应利用丙二酸半硫酯作为简单的酯替代物。提议在机理中亲核加成先于脱羧作用，已通过使用电喷雾电离（ESI）质谱分析和DFT计算来鉴定中间体，对此进行了详细研究。

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《Chemistry: A European journal》 |2011年第30期|共8页
作者
Pan Y.; Kee C.W.; Jiang Z.; Ma T.; Zhao Y.; Yang Y.; Xue H.; Tan C.-H.;
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正文语种 eng
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amination; biomimetic synthesis; decarboxylation; density functional calculations; Mannich reaction; organocatalysis;

机译：胺化仿生合成脱羧密度泛函曼尼希反应有机催化;

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专利

1. Expanding the Utility of Br?nsted Base Catalysis: Biomimetic Enantioselective Decarboxylative Reactions [J] . Yuanhang Pan, Choon Wee Kee, Prof. Zhiyong Jiang, Chemistry - A European Journal . 2011,第30期

机译：扩大布朗斯台德碱催化的效用：仿生对映选择性脱羧反应
2. Highlights in Organic Chemistry [ Recent Breakthroughs in Enantioselective Brφnsted Acid and Brφnsted Base Catalysis ] [J] . Petri M. Pihko Letters in Organic Chemistry . 2005,第5期

机译：有机化学亮点[对映选择性布朗斯台德酸和布朗斯台德碱催化的最新突破]
3. Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/ Chiral Br?nsted Acid Cooperative Catalysis [J] . SCOTT E. DENMARK, MATTHEW T. BURK Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry . 2014,第7期

机译：Lewis碱/手性布朗斯台德酸协同催化对映选择性溴环醚化反应的机理及机理
4. Asymmetric Hetero-Diels–Alder Reaction of Non-activated Substrates Utilizing Dual Activation of Cationic Fe(III) Lewis Acid and Chiral Br?nsted Acid [C] . Rei Tomifuji, Takuya Kurahashi, Seijiro Matsubara 日本化学会春季年会講演予稿集 . 2018

机译：利用阳离子Fe（III）Lewis酸和手性β的非活化基材的不对称异质蛋白 - 桤木反应。
5. Enantioselective Brønsted acid-catalyzed reaction methodology. Part A: Enantioselective Mannich reaction. Part B: Enantioselective desymmetrization of meso-aziridines [D] . Rowland, Emily Bretherick 2008

机译：对映选择性布朗斯台德酸催化的反应方法。 A部分：对映选择性曼尼希反应。 B部分：内消旋氮丙啶的对映选择性去对称化
6. Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/Chiral Brønsted Acid Cooperative Catalysis [O] . SCOTT E. DENMARK, MATTHEW T. BURK -1

机译：Lewis碱/手性布朗斯台德酸协同催化对映选择性溴环醚化反应的机理及机理
7. Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/Chiral Brønsted Acid Cooperative Catalysis [O] . Scott E. Denmark, Matthew T. Burk 2013

机译：通过路易斯碱/手性Brønsted酸合作催化反应和机制对映选择性溴环醚化反应的影响

Expanding the utility of Br?nsted base catalysis: Biomimetic enantioselective decarboxylative reactions

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