Asymmetric a-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide

Minami Odagi; Kota Furukori; Tatsuya Watanabe; Kazuo Nagasawa

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Asymmetric a-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide

机译：存在氢过氧化异丙苯的胍尿素双官能有机催化剂对四氢酮衍生的β-酮酸酯的不对称α-羟基化反应

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Highly enantioselective catalytic oxidation of 1-tetralone-derived b-keto esters was achieved by using a guanidine-urea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP), a safe, commercially available oxidant. The a-hydroxylation products were obtained in 99% yield with up to 95% enantiomeric excess (ee). The present oxidation was successfully applied to synthesize a key intermediate of the anti-cancer agent daunorubicin (2).

机译：通过使用胍-脲双功能有机催化剂在安全，可商购获得的异丙苯氢过氧化物（CHP）的存在下，实现了1-四氢萘酮衍生的β-酮酯的高度对映选择性催化氧化。以99％的产率获得α-羟基化产物，对映体过量高达95％（ee）。本氧化法成功地用于合成抗癌药柔红霉素的关键中间体（2）。

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《Chemistry: A European journal》 |2013年第49期|共6页
作者
Minami Odagi; Kota Furukori; Tatsuya Watanabe; Kazuo Nagasawa;
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正文语种 eng
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关键词
esters; enantioselectivity; hydroxylation; organocatalysis; oxidation; synthetic methods;

机译：酯;对映选择性;羟基化;有机催化;氧化;合成方法;

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1. Asymmetric a-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide [J] . Minami Odagi, Kota Furukori, Tatsuya Watanabe, Chemistry: A European journal . 2013,第49期

机译：存在氢过氧化异丙苯的胍尿素双官能有机催化剂对四氢酮衍生的β-酮酸酯的不对称α-羟基化反应
2. Asymmetric a-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide [J] . Minami Odagi, Kota Furukori, Tatsuya Watanabe, Chemistry: A European journal . 2013,第49期

机译：存在氢过氧化异丙苯的胍尿素双官能有机催化剂对四氢酮衍生的β-酮酸酯的不对称α-羟基化反应
3. Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution [J] . Minami Odagi, Kota Furukori, Yoshiharu Yamamoto, Journal of the American Chemical Society . 2015,第5期

机译：鸟嘌呤-Bisurea双功能有机催化剂中立体控制的起源，可促进四氢酮衍生的β-酮酸酯的α-羟基化：通过有机催化氧化动力学拆分法合成β-和γ-取代的四氢酮衍生物
4. Asymmetric Cycloetherification via Cyanation of Acylsilanes Using Bifunctional Organocatalysts [C] . Akira Matsumoto, Keisuke Asano, Seijiro Matsubara 日本化学会春季年会講演予稿集 . 2018

机译：使用双官能有机催化剂通过酰基硅烷化的不对称环氧醚化
5. Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters [O] . Minami Odagi, Kan Takayama, Makoto Sato, 2015

机译：具有手性吡咯烷部分的胍-Bisurea双功能有机催化剂的开发及其在四氢酮衍生的β-酮酯的α-羟基化反应中的应用
6. Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters [O] . Minami Odagi, Kan Takayama, Makoto Sato, 2015

机译：手性吡咯烷分子胍 - 双脲双功能有机催化剂的研制及其对四氢萘酮衍生的β-酮酯的α-羟基化反应的应用

Asymmetric a-Hydroxylation of Tetralone-Derived β-Ketoesters by Using a Guanidine-Urea Bifunctional Organocatalyst in the Presence of Cumene Hydroperoxide

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