Mild Synthesis of beta-Amino-alpha,alpha-difluoro Ketones from Acylsilanes and Trifluoromethyltrimethylsilane in a One-Pot Imino Aldol Reaction

Sylvain Jonet; Franck Cherouvrier; Charles Portella; Thierry Brigaud

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Mild Synthesis of beta-Amino-alpha,alpha-difluoro Ketones from Acylsilanes and Trifluoromethyltrimethylsilane in a One-Pot Imino Aldol Reaction

机译：一锅氨基羟醛反应中由酰基硅烷和三氟甲基三甲基硅烷轻度合成β-氨基-α，α-二氟酮

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beta-Amino-alpha,alpha-difluoro ketones have been very conveniently prepared in a one-pot procedure from acylsilanes,trifluoro-methyltrimethylsilane and imines.The key intermediate in this reaction is a difluoroenoxysilane.The Lewis acid promoted imino aldol reaction was performed with BF_3 centre dot OEt_2 or under very mild conditions using a catalytic amount of Yb(OTf)_3.The reaction with chiral benzylimines occurred in good yield with 52-78 % de.Palladium-catalyzed hydro-genolysis furnished an unprotected beta-amino-alpha,alpha-difluoro ketone or a beta-amino-alpha,alpha-difluoro alcohol.

机译：一锅法很容易地由酰基硅烷，三氟甲基三甲基硅烷和亚胺制备β-氨基-α，α-二氟酮。该反应的关键中间体是二氟烯氧基硅烷。路易斯酸促进的亚氨基羟醛反应与BF_3中心点OEt_2或在非常温和的条件下使用催化量的Yb（OTf）_3。与手性苄基亚胺的反应收率高达52-78％。钯催化的氢解提供了未保护的β-氨基-α ，α-二氟酮或β-氨基-α，α-二氟醇。

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《European journal of organic chemistry》 |2005年第20期|共9页
作者
Sylvain Jonet; Franck Cherouvrier; Charles Portella; Thierry Brigaud;
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正文语种 eng
中图分类有机化学;
关键词
Imino aldol reaction; Amino ketones; Fluorine; Silicon; Silyl enol ether;

机译：亚胺基羟醛反应;氨基酮;氟;硅;甲硅烷基烯醇醚;

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1. Mild Synthesis of beta-Amino-alpha,alpha-difluoro Ketones from Acylsilanes and Trifluoromethyltrimethylsilane in a One-Pot Imino Aldol Reaction [J] . Sylvain Jonet, Franck Cherouvrier, Charles Portella, European journal of organic chemistry . 2005,第20期

机译：一锅氨基羟醛反应中由酰基硅烷和三氟甲基三甲基硅烷轻度合成β-氨基-α，α-二氟酮
2. Chalcone and cinnamate synthesis via one-pot enol silane formation-Mukaiyama aldol reactions of ketones and acetate esters [J] . Downey C. Wade, Glist Hadleigh M., Takashima Anna, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2018,第32期

机译：Chalcone和肉桂醛合成通过单壶烯醇硅烷形成-Mukaiyama aldol酮和醋酸酯的反应
3. A new synthesis of pyrrolidines via imino-aldol reaction of (2-trimethylsilylmethyl)cyclopropyl ketones with imines [J] . Veejendra K.Yadav, Archana Gupta Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2008,第20期

机译：通过（2-三甲基甲硅烷基甲基）环丙基酮与亚胺的亚氨基羟醛反应合成吡咯烷的新方法
4. Enantioselective 2+2 Cycloaddition Reaction of 1-Methoxyallenylsilane with alpha-Imino Ester:Chiral Synthesis of alpha,beta-Unsaturated Acylsilanes [C] . Kazunori Daidouji, Kohei Fuchibe, Takahiko Akiyama Symposium on Organometallic Chemistry . 2003

机译：1-甲氧基亚乙烷与α-亚氨基酯的映选择性2 + 2环加入反应：α，β-不饱和酰基硅烷的手性合成
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. One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakurai and Aldol Reactions [O] . Chan Woo Huh, Gagandeep K. Somal, Christopher E. Katz, -1

机译：使用多米诺反应的内酰胺的单壶合成：Schmidt与Sakurai和Aldol反应的组合
7. Tandem Bis-aldol Reaction of Ketones: A Facile One-Pot Synthesis of 1,3-Dioxanes in Aqueous Medium [O] . -1

机译：酮酮的双醛 - 酮反应：含水介质中1,3-二氧烷的容易一罐合成

Mild Synthesis of beta-Amino-alpha,alpha-difluoro Ketones from Acylsilanes and Trifluoromethyltrimethylsilane in a One-Pot Imino Aldol Reaction

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