Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes

Takuya Hashimoto; Hisashi Miyamoto; Yuki Naganawa; Keiji Maruoka

首页> 外文期刊>Journal of the American Chemical Society >Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes

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Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes

机译：通过α-烷基-α-重氮羰基化合物与醛之间的不对称氧化还原C-C键形成立体选择性合成α-烷基-β-酮酰亚胺

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摘要

Asymmetric Claisen condensation of chiral imide enolates and acyl halides reported by Evans et al. in 1984 succeeded in shedding new light on the property of chiral nonracemic α-alkyl-β-keto imides, wherein condensation products could be isolated without epimerization due to the low kinetic acidity of the α-hydrogen (eq 1). Although several landmark studies on its application in the preparation of complex polyol side chains underlined the synthetic value of this method, the requirement of two activated reaction partners for the C-C bond formation would become a limitation in the cases where the reactions use substrates with labile functionalities.

机译：Evans等报道了手性酰亚胺烯酸酯和酰基卤的不对称Claisen缩合。 1984年，成功地揭示了手性非外消旋α-烷基-β-酮基酰亚胺的性质，由于α-氢的低动力学酸度（等式1），可以分离出缩合产物而没有差向异构化。尽管对其在复杂多元醇侧链制备中的应用进行了几项具有里程碑意义的研究，突显了该方法的合成价值，但在反应使用功能不稳定的底物的情况下，需要两个活化的反应伙伴来形成CC键。

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来源
《Journal of the American Chemical Society》 |2009年第32期|11280-11281|共2页
作者
Takuya Hashimoto; Hisashi Miyamoto; Yuki Naganawa; Keiji Maruoka;
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作者单位

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan;

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan;

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan;

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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2. Catalytic Asymmetric Roskamp Reaction of α-Alkyl-α-diazoesters with Aromatic Aldehydes: Highly Enantioselective Synthesis of α-Alkyl-β-keto Esters [J] . Wei Li Jun Wang Xiaolei Hu Ke Shen Wentao Wang Yangyang Chu Lili Lin Xiaohua Liu and Xiaoming Feng Journal of the American Chemical Society . 2010,第25期

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4. Mechanism of Solid Acid Catalyzed C-C Bond Formation and Oxygen Removal from Aldehydes [C] . Fan Lin, Ya-Huei (Cathy) Chin AIChE annual meeting . 2012

机译：固体酸催化醛键形成C-C键和除氧机理
5. Exploration of alpha-Diazocarbonyl Compounds for Transition-Metal Catalyzed Carbon-Carbon Bond Formations. Development of Palladium-Catalyzed Stereoselective Synthesis of Trisubstituted Alkenes and the Synthesis of Quaternary alpha,alpha-Heterodiaryl Carboxylic Acids by Rhodium-Catalyzed Multi-Component Coupling Reactions. [D] . Tsoi, Yuk Tai. 2012

机译：探索用于过渡金属催化的碳-碳键形成的α-重氮羰基化合物。铑催化的多组分偶合反应在钯催化的立体选择性合成三取代的烯烃上的发展和季铵的α，α-杂二芳基羧酸的合成。
6. The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde [O] . Jared K. Nelson, Brendan Twamley, Trinidad J. Villalobos, -1

机译：烷基和芳基锌试剂向异恶唑醛的催化不对称加成
7. The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde [O] . Jared K. Nelson, Brendan Twamley, Trinidad J. Villalobos, 2008

机译：将烷基和芳基 - 锌试剂加入异恶唑醛的催化不对称

Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes

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