The indium(III) chloride-catalysed hydrolysis and in situ Mukaiyama-type reaction of arylmethyl ketone derived silyl enol ethers under solvent-free conditions

2003 ◽  
Vol 44 (30) ◽  
pp. 5683-5685 ◽  
Author(s):  
Sirirat Chancharunee ◽  
Patrick Perlmutter ◽  
Maya Statton
Keyword(s):  
Solvent Free ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Type Reaction ◽  
Solvent Free Conditions

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.

Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Trifluoromethanesulfonate-Catalyzed Allylation of Dioxolanes

2008 ◽  
Vol 61 (6) ◽  
pp. 419 ◽  
Author(s):  
Matthew J. Spafford ◽  
James E. Christensen ◽  
Matthew G. Huddle ◽  
Joshua R. Lacey ◽  
Ram S. Mohan
Keyword(s):  
Organic Synthesis ◽  
Multicomponent Reaction ◽  
Scale Up ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Bismuth Compounds ◽  
Solvent Free Conditions ◽  
In Situ Derivatization

A bismuth trifluoromethanesulfonate (triflate)-catalyzed (2.0 mol-%) multicomponent reaction involving the allylation of dioxolanes followed by in situ derivatization with anhydrides to generate highly functionalized esters has been developed under solvent-free conditions. Most reagents used to date for allylation of dioxolanes are highly corrosive and are often required in stoichiometric amounts. In contrast, the use of a relatively non-toxic and non-corrosive bismuth(iii)-based catalyst makes this methodology especially attractive for scale-up.

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