Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

Ishizawa Kouhei; Nagai Hideoki; Shimizu Yohei; Kanai Motomu

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Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

机译：硼催化的羧酸选择性醛醇与三氟甲基酮反应

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A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the a-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.

机译：开发了与三氟甲基酮的催化羧酸选择性醛醇反应。硼催化剂和羧酸之间的可逆和选择性共价键形成是实现简单羧酸的前所未有的催化醛醇反应的关键。即使在供体基材中的酮，酯或酰胺官能团存在下，反应也在羧酸的A-位置进行化学胶合。通过吲哚美辛和三乙酰胆酸的转化，化学选择性对生物学相关化合物的后期衍生化有益。

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《Chemical and Pharmaceutical Bulletin》 |2018年第3期|共4页
作者
Ishizawa Kouhei; Nagai Hideoki; Shimizu Yohei; Kanai Motomu;
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作者单位

Univ Tokyo Grad Sch Pharmaceut Sci Bunkyo Ku 7-3-1 Hong Tokyo 1130033 Japan;

Univ Tokyo Grad Sch Pharmaceut Sci Bunkyo Ku 7-3-1 Hong Tokyo 1130033 Japan;

Univ Tokyo Grad Sch Pharmaceut Sci Bunkyo Ku 7-3-1 Hong Tokyo 1130033 Japan;

Univ Tokyo Grad Sch Pharmaceut Sci Bunkyo Ku 7-3-1 Hong Tokyo 1130033 Japan;

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原文格式 PDF
正文语种 eng
中图分类药学;化学;
关键词
carboxylic acid; aldol reaction; boron catalyst; trifluoromethyl ketone;

机译：羧酸;醛醇反应;硼催化剂;三氟甲基酮;

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专利

1. Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones [J] . Kouhei Ishizawa, Hideoki Nagai, Yohei Shimizu, Chemical and Pharmaceutical Bulletin . 2018,第3期

机译：硼催化的羧酸选择性醛醇与三氟甲基酮反应
2. Aldol Reactions of Ketone Donors with Aryl Trifluoromethyl Ketone Acceptors Catalyzed by 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) for Concise Access to Aryl- and Trifluoromethyl-Substituted Tertiary Alcohols [J] . Zhang Dongxin, Tanaka Fujie Advanced synthesis & catalysis . 2015,第16a17期

机译：1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）催化的酮供体与芳基三氟甲基酮受体的醛醇缩合反应，用于简捷地获得芳基和三氟甲基取代的叔醇
3. ASYMMETRIC ALDOL REACTIONS OF TRIFLUOROMETHYL KETONES WITH A CHIRAL NI(II) COMPLEX OF GLYCINE - STEREOCONTROLLING EFFECT OF THE TRIFLUOROMETHYL GROUP [J] . Soloshonok VA., Kukhar VP., Avilov DV. Tetrahedron . 1996,第38期

机译：三氟甲基酮与甘氨酸手性镍（II）配合物的不对称ALDOL反应-三氟甲基的立体控制作用
4. Double Stereodifferentiating Studies in Boron-Mediated Aldol Reactions of Chiral Methyl Ketones and Chiral Aldehydes [C] . Savio Moita Pinheiro, Andrea Maria Aguilar, Luiz Carlos Dias European Symposium on Organic Chemistry . 2009

机译：硼介导的手性甲基酮和手性醛反应的双立体二氧化性研究
5. I. Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates. II. Diastereoselective de novo synthesis of pentasubstituted γ-butyrolactones from silyl glyoxylates and ketones via double Reformatsky reactions. III. Progress toward the total synthesis of leustroducsin B [D] . Greszler, Stephen Nathaniel 2010

机译：I.甲硅烷基乙醛酸酯的催化氧化还原引发的乙醇酸酯醛醇加成物。二。通过双重Reformatsky反应从甲硅烷基乙醛酸酯和酮进行非对映选择性从头合成五取代的γ-丁内酯。三，全合成杜鹃花素B的研究进展
6. Enantio- and Diastereoselective Synthesis of syn-β-Hydroxy-α-Vinyl Carboxylic Esters via Reductive Aldol Reactions of Ethyl Allenecarboxylate with 10-TMS-9-Borabicyclo3.3.2decane and DFT Analysis of the Hydroboration Pathway [O] . Jeremy Kister, Daniel H. Ess, William R. Roush -1

机译：通过烯丙基羧酸乙酯与10-TMS-9-硼环3.3.2癸烷的还原性醛醇缩合反应和氢硼化途径的DFT分析对映体和非对映体选择性合成Syn-β-羟基-α-乙烯基羧酸酯
7. Siloxy Esters as Traceless Activator of Carboxylic Acids: Boron-Catalyzed Chemoselective Asymmetric Aldol Reaction [O] . Taiki Fujita, Mina Yamane, W. M. C. Sameera, 2021

机译：硅氧烷酯作为羧酸的无甜叶活化剂：硼催化的化学选择性不对称醛醇反应

Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

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