Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals

Yoshihiro Inamoto; Yuta Kaga; Yoshihiro Nishimoto; Makoto Yasuda; Akio Baba

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Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals

机译：三卤化镓催化使用甲硅烷基氰化物和丁烯基乙缩醛将两种不同的亲核碳原子顺序加成到酯中

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摘要

A sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β-cyano-β-siloxy esters. This is the first example of the sequential addition of two different carbon nucleophiles to esters. The employment of lactones provided α,α-disubstituted cyclic ethers with a cyano group and an ester moiety. A variety of esters and lactones are applicable to this reaction system.

机译：通过三卤化镓催化剂实现将甲硅烷基氰化物和乙烯酮甲硅烷基乙缩醛顺序添加到酯中以生产β-氰基-β-甲硅烷氧基酯。这是将两个不同的碳亲核试剂顺序加成到酯中的第一个例子。内酯的使用提供了具有氰基和酯部分的α，α-二取代的环状醚。多种酯和内酯可用于该反应系统。

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《Chemistry: A European journal》 |2014年第37期|共5页
作者
Yoshihiro Inamoto; Yuta Kaga; Yoshihiro Nishimoto; Makoto Yasuda; Akio Baba;
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正文语种 eng
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esters; gallium; lactones; silicon; synthetic methods;

机译：酯;镓;内酯;硅;合成方法;

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1. Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals [J] . Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Chemistry: A European journal . 2014,第37期

机译：三卤化镓催化使用甲硅烷基氰化物和丁烯基乙缩醛将两种不同的亲核碳原子顺序加成到酯中
2. Mukaiyama Aldol Reaction of Ester Acceptors:Organoaluminums Catalyze Nucleophilic Addition of Ketene Silyl Acetals [J] . Shin Iwata, Toshiyuki Hamura, Takashi Matsumoto Chemistry Letters . 2007,第4期

机译：酯受体的Mukaiyama Aldol反应：有机铝催化乙烯-甲硅烷基缩醛的亲核加成
3. The Copper(I) Chloride-Catalyzed Reaction of Ketene Silyl Acetals or Silyl Enol Ethers with α-Halogen Substituted Allylsilanes to Form Carbonyl Compounds Bearing Vinylsilane Functionality [J] . Michiharu Mitani Masayuki Masuda Letters in Organic Chemistry . 2007,第3期

机译：铜（I）催化的乙炔甲硅烷基缩醛或甲硅烷基烯醇醚与α-卤素取代的烯丙基硅烷的反应形成具有乙烯基硅烷官能团的羰基化合物
4. ADDITION OF NITRONES TO SILYL KETENE ACETALS CATALYZED BY LANTHANIDE TRIFLATES [C] . Changtao Qian International symposium for Chinese organic chemists . 2000

机译：向含镧系元素催化的甲硅烷基乙烯缩醛加入硝酸盐
5. Studies in asymmetric catalysis: Lewis base catalyzed, enantioselective addition of trimethylsilyl cyanide, trimethylsilyltrifluoromethane, and glycolate-derived silyl ketene acetals to aldehydes [D] . Chung, Won-Jin 2008

机译：不对称催化的研究：路易斯碱催化，对映选择性地将三甲基甲硅烷基氰化物，三甲基甲硅烷基三氟甲烷和乙醇酸衍生的甲硅烷基烯酮缩醛加成醛
6. Iridium-Catalyzed Enantioselective Allylic Substitutions of Aliphatic Esters via Silyl Ketene Acetals [O] . Xingyu Jiang, Prof. John F. Hartwig -1

机译：铱催化的甲硅烷基乙缩醛对脂肪族酯的对映选择性烯丙基取代
7. ASYMMETRIC CROSS ALDOL SYNTHESIS. ASYMMETRIC ADDITION OF SILYL ENOL ETHER AND KETENE SILYL ACETAL TO α-KETO ESTERS [O] . Iwao Ojima, Katsuhiko Yoshida, Shin-ichi Inaba 1977

机译：不对称的交叉醛醇合成。向α-酮酯的甲硅烷基烯醇醚和酮甲硅烷基缩醛的不对称添加

Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals

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