HClO4 catalysed aldol-type reaction of fluorinated silyl enol ethers with acetals or ketals toward fluoroalkyl ethers

2019 ◽  
Vol 17 (43) ◽  
pp. 9430-9434 ◽  
Author(s):  
You-Ping Tian ◽  
Yi Gong ◽  
Xiao-Si Hu ◽  
Jin-Sheng Yu ◽  
Ying Zhou ◽  
...  
Keyword(s):  
Enol Ethers ◽  
Silyl Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Type Reaction ◽  
Highly Efficient ◽  
Enol Silyl Ethers

A highly efficient metal-free catalytic aldol-type reaction of fluorinated enol silyl ethers and acetals/ketals toward functionalized fluoroalkyl ethers is developed by using less than 1.0 mol% HClO4 (70 wt%, aq.).

Organocatalytic enantioselective Mukaiyama–Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines

2016 ◽  
Vol 3 (3) ◽  
pp. 298-303 ◽  
Author(s):  
Jin-Sheng Yu ◽  
Jian Zhou
Keyword(s):  
Amino Acid ◽  
Mannich Reaction ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Enol Ethers ◽  
Silyl Ethers ◽  
Silyl Enol Ethers ◽  
Catalytic Asymmetric ◽  
Enol Silyl Ethers

The first catalytic asymmetric Mukaiyama–Mannich reaction of fluorinated silyl enol ethers and ketimines is developed, allowing highly enantioselective synthesis of benzosultam based β-fluorinated Cα-tetrasubstituted α-amino acid derivatives.

ChemInform Abstract: Zinc Tetrafluoroborate Catalyzed Mannich-Type Reaction of Aldimines and Silyl Enol Ethers in Aqueous Medium.

ChemInform ◽  
2010 ◽  
Vol 33 (28) ◽  
pp. no-no
Author(s):  
Brindaban C. Ranu ◽  
Sampak Samanta ◽  
Sankar K. Guchhait
Keyword(s):  
Aqueous Medium ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Type Reaction

Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction

2001 ◽  
Vol 66 (12) ◽  
pp. 1735-1745 ◽  
Author(s):  
Andrei V. Malkov ◽  
Benjamin P. Farn ◽  
Nigel Hussain ◽  
Pavel Kočovský
Keyword(s):  
Allylic Substitution ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Type Reaction ◽  
Bond Forming ◽  
Glycal Acetates ◽  
Glycosylation Reaction

The mild, Lewis-acidic complexes [Mo(CO)4Br2]2, (MeCN)2Mo(CO)3(SnCl3)Cl, and (acac)2Mo(OTf)2 have been found to catalyze the C(1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2 : 1 to 4 : 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2 : 1 to 3 : 1) in a thermodynamically controlled process.

Highly Efficient Access to Both Geometric Isomers of Silyl Enol Ethers: Sequential 1,2-Brook/Wittig Reactions

2016 ◽  
Vol 128 (34) ◽  
pp. 10233-10236
Author(s):  
Yuji Matsuya ◽  
Kentaro Wada ◽  
Daishiro Minato ◽  
Kenji Sugimoto
Keyword(s):  
Geometric Isomers ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Highly Efficient ◽  
Efficient Access ◽  
Wittig Reactions

Thermal rearrangement of functionalized 1,2-divinylcyclopropane systems. A convenient synthesis of substituted 4-cyclohepten-1-ones

1986 ◽  
Vol 64 (1) ◽  
pp. 180-187 ◽  
Author(s):  
Edward Piers ◽  
Max S. Burmeister ◽  
Hans-Ulrich Reissig
Keyword(s):  
Acid Hydrolysis ◽  
The Other ◽  
Thermal Rearrangement ◽  
Enol Ethers ◽  
Acyl Chlorides ◽  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers ◽  
Hydrolysis Of ◽  
Subsequent Acid

Reaction of the acyl chlorides 14–21 with lithium (phenylthio)(cis-2-vinylcyclopropyl)cuprate (2) provided the ketones 22–29. Compounds 22–25, upon treatment with i-Pr2NLi-Me3SiCl, were converted cleanly into the enol silyl ethers 30–33, which gave the 1,4-cycloheptadienes 34–37 upon thermolysis (100–110 °C). Acid hydrolysis of the latter materials produced the corresponding 4-cyclohepten-1-ones 38–41. However, subjection of the cis-2-vinylcyclopropyl ketones 26–29 to i-Pr2NLi-t-BuMe2SiCl afforded, in each case, a mixture of isomeric enol ethers (26 → 42 + 44 (1:1); 27 → 43 + 45 (1:9); 28 → 56 + 58 (1:1); 29 → 57 + 59 (4:1)). Thermolysis (150–175 °C) of these mixtures, followed by acid hydrolysis of the resultant products, gave the 4-cyclohepten-1-ones 54, 55, 64, and 65, admixed with the corresponding 3-methylenecyclopentenes 52, 53, 62, and 63. On the other hand, treatment of the trans-2-vinylcyclopropyl ketones 70–74 with i-Pr2NLi–t-BuMe2SiCl provided exclusively or predominantly the enol ethers 75–79. Thermolysis (230 °C) of the latter materials and subsequent acid hydrolysis of the resultant products 80, 50, 51, 60, and 61 afforded the 4-cyclopenten-1-ones 38, 54, 55, 64, and 65.

Trimethylsilyl trifltate catalyzed aldol-type reaction of enol silyl ethers and acetals or related compounds

Tetrahedron ◽  
1988 ◽  
Vol 44 (13) ◽  
pp. 4259-4275 ◽  
Author(s):  
Shizuaki Murata ◽  
Masaaki Suzuki ◽  
Ryoji Noyori
Keyword(s):  
Silyl Ethers ◽  
Type Reaction ◽  
Enol Silyl Ethers ◽  
Related Compounds
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