alpha,alpha-Difluoro-alpha-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

Honraedt Aurelien; Van Der Lee Arie; Campagne Jean-Marc; Leclerc Eric

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alpha,alpha-Difluoro-alpha-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

机译：α，α-二氟 - α-（三甲基甲硅烷基）乙酰胺作为用于制备二氟化醛醇和曼尼希加合物的多种试剂

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摘要

The very efficient addition of alpha,alpha-difluoro-alpha-(trimethylsilyl)acetamides to aldehydes, ketones and N-(tert-butanesulfinyl)imines is described. The reaction is promoted by a catalytic amount of tetran- butylammonium diphenyltrifluorosilicate (TBAT) and high yields, as well as very high stereoselectivities in the case of N-(tert-butanesulfinyl)imines, are achieved. The synthetic potential of this method is illustrated by the conversion of the resulting products to beta-hydroxy ketones, diols and beta-amino alcohols by addition of various Grignard reagents or reduction of the amide moiety.

机译：描述了对醛，酮和N-（叔丁磺酰基）亚胺的非常有效地加入α，α-二氟-α-（三甲基甲硅烷基）乙酰胺。通过催化量的催化量的二苯基三氟硅酸盐（TBAT）和高产率的催化量促进反应，以及在N-（叔丁磺酰基）亚胺的情况下非常高的立体切性。通过添加各种格子试剂或减少酰胺部分，通过加入各种格氏试剂或减少酰胺部分，通过将所得产物转化为β-羟基酮，二醇和β-氨基醇来说明该方法的合成电位。

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来源
《Advanced synthesis & catalysis》 |2017年第16期|共9页
作者
Honraedt Aurelien; Van Der Lee Arie; Campagne Jean-Marc; Leclerc Eric;
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作者单位

ENSCM CNRS UMR 5253 Inst Charles Gerhardt UM2 UM1 8 Rue Ecole Normale F-34296 Montpellier 5 France;

ENSCM UMII CNRS Inst Europeen Membranes UMR 5635 Pl Eugene Bataillon CC 047 F-34095 Montpellier 5 France;

ENSCM CNRS UMR 5253 Inst Charles Gerhardt UM2 UM1 8 Rue Ecole Normale F-34296 Montpellier 5 France;

ENSCM CNRS UMR 5253 Inst Charles Gerhardt UM2 UM1 8 Rue Ecole Normale F-34296 Montpellier 5 France;

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原文格式 PDF
正文语种 eng
中图分类化学工业;物理化学（理论化学）、化学物理学;化学反应过程;
关键词
aldol reaction; diastereoselectivity; fluorine; Grignard reagents; Mannich reaction;

机译：aldol反应;非对映选择;氟;格氏试剂;曼尼希反应;

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2. 聚乙二醇和十六烷基三甲基溴化铵对碱性电池中锌和Zn-Ni合金腐蚀的协同抑制作用 [J] . Hany M.ABD EL-LATEEF, Mahmoud ELROUBY 中国有色金属学报：英文版 . 2020,第001期
3. alpha,alpha-Difluoro-alpha-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts [J] . Honraedt Aurelien, Van Der Lee Arie, Campagne Jean-Marc, Advanced synthesis & catalysis . 2017,第16期

机译：α，α-二氟 - α-（三甲基甲硅烷基）乙酰胺作为用于制备二氟化醛醇和曼尼希加合物的多种试剂
4. The use of bis(trimethylsilyl) acetamide and bis(trimethylsilyl) urea for protection and as control reagents in synthesis [Review] [J] . El Gihani MT., Heaney H. Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 1998,第4期

机译：双（三甲基甲硅烷基）乙酰胺和双（三甲基甲硅烷基）尿素在合成中的保护和控制试剂用途[综述]
5. Preparations of Z-alpha,beta-unsaturated amides by using Horner-Wadsworth-Emmons reagents, (diphenylphosphono)acetamides [J] . Ando K. Synlett . 2001,第8期

机译：通过使用Horner-Wadsworth-Emmons试剂（二苯基膦基）乙酰胺制备Z-α，β-不饱和酰胺
6. Catalytic enantioselective synthesis of O-and N-substituted quaternary carbon stereogenic centers: 1. Aluminum-catalyzed alkylations of alpha-ketoesters with dialkylzinc reagents. 2. Silver-catalyzed vinylogous Mannich-type reactions of alpha-ketoimine esters with siloxyfurans [D] . Wieland, Laura Caroline 2008

机译：O和N取代的季碳立构中心的催化对映选择性合成：1.用二烷基锌试剂进行铝催化的α-酮酸酯的烷基化。 2.α-酮亚胺酯与甲硅烷氧基呋喃的银催化乙烯基曼尼希型反应
7. Hydrothermal Preparation and Characterization of Ultralong Strontium-Substituted Hydroxyapatite Whiskers Using Acetamide as Homogeneous Precipitation Reagent [O] . Jianqiang Xu, Yaoqi Yang, Rong Wan, -1

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8. Reactions of 2-Chloroacyltrimethylsilanes with Grignard Reagents. Preparation of 3-(Trimethylsilyl)-2-alkanones and 2-(Trimethylsilyl)-1-alkanols [O] . Toshio Sato, Kazuhisa Matsumoto, Toru Abe, 1984

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9. Palladium Catalyzed Coupling of F-Vinyl Zinc Reagents with Aryl Iodides. An Improved Synthesis of Alpha, Beta, Beta-Trifluorostyrenes and the Stereospecific Preparation of 1-Phenyl-F-Propenes [R] . Heinze, P. L., Burton, D. J. 1986

机译：钯催化F-乙烯基锌试剂与芳基碘化物的偶联。 α，β，β-三氟苯乙烯的改进合成及1-苯基-F-丙烯的立体特异性制备

alpha,alpha-Difluoro-alpha-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

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