Enantioselective Nitroso-Diels–Alder Reaction and Its Application for the Synthesis of (-)-Peracetylated Conduramine A-1

Chandan Kumar Jana; Stefan Grimme; Armido Studer

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Enantioselective Nitroso-Diels–Alder Reaction and Its Application for the Synthesis of (-)-Peracetylated Conduramine A-1

机译：对映选择性亚硝基-Diels-Alder反应及其在（-）-过乙酰化Conduramine A-1合成中的应用

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CuI-catalyzed enantioselective nitroso-Diels–Alder reactions (NDA reactions) of 2-nitrosopyridine with various dienes are presented. The [CuPF6ACHTUNGTRENUNG(MeCN)4]/Walphos-CF3 catalyst system is best suited to catalyze the NDA reaction of various dienes by using 2-nitrosopyridine as a dienophile. In most of the cases studied, ycloadducts are obtained in quantitative yield with very good to excellent enantioselectivities. Based on DFT calculations, a model to explain the stereochemical outcome of the NDA reaction is presented. Finally, an efficient short synthesis of (-)-peracetylated conduramineA-1 by applying the enantioselective NDA reaction as a key step is described.

机译：提出了CuI催化的2-亚硝基吡啶与各种二烯的对映选择性亚硝基-Diels-Alder反应（NDA反应）。 [CuPF6ACHTUNGTRENUNG（MeCN）4] / Walphos-CF3催化剂体系最适合通过使用2-亚硝基吡啶作为双亲物来催化各种二烯的NDA反应。在大多数研究的情况下，高通量化合物的定量收率很高，对映选择性非常好。基于DFT计算，提出了解释NDA反应的立体化学结果的模型。最后，描述了通过应用对映选择性NDA反应作为关键步骤的有效的短合成（-）-过乙酰化的conduramineA-1。

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《Chemistry: A European journal》 |2009年第36期|共7页
作者
Chandan Kumar Jana; Stefan Grimme; Armido Studer;
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正文语种 eng
中图分类应用化学;
关键词
copper; density functionalcal culations; Diels–Alder reaction; enantioselective catalysis; natural products;

机译：铜;密度泛函计算;狄尔斯-阿尔德反应;对映选择性催化;天然产物;

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1. Enantioselective Nitroso-Diels–Alder Reaction and Its Application for the Synthesis of (-)-Peracetylated Conduramine A-1 [J] . Chandan Kumar Jana, Stefan Grimme, Armido Studer Chemistry: A European journal . 2009,第36期

机译：对映选择性亚硝基-Diels-Alder反应及其在（-）-过乙酰化Conduramine A-1合成中的应用
2. Synthesis and application of novel imidazole and 1H-tetrazolic acid containing catalysts in enantioselective organocatalyzed Diels-Alder reactions [J] . Hartikka A, Hojabri L, Bose PP, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2009,第16期

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5. Synthetic applications of the type 2 intramolecular Diels-Alder reaction: (1) Efforts toward the total synthesis of the welwitindolinone alkaloids and (2) Enantioselective synthesis of bridged bicyclic ring systems. [D] . Brailsford, John A. 2009

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Enantioselective Nitroso-Diels–Alder Reaction and Its Application for the Synthesis of (-)-Peracetylated Conduramine A-1

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