Homolytic aldol reactions: thiol-catalysed radical-chain addition of aldehydes to enol esters and to sily enol ethers

1996 ◽  
pp. 2201 ◽  
Author(s):  
Hai-Shan Dang ◽  
Brian P. Roberts
Keyword(s):  
Aldol Reactions ◽  
Radical Chain ◽  
Enol Ethers ◽  
Enol Esters

scholarly journals Radical Chain Monoalkylation of Pyridines

2021 ◽  
Author(s):  
Samuel Rieder ◽  
Camilo Meléndez ◽  
Kleni Mulliri ◽  
Philippe Renaud
Keyword(s):  
Rate Constant ◽  
Iodine Atom ◽  
Radical Chain ◽  
Enol Ethers ◽  
Alkyl Radicals ◽  
Reaction Proceeds ◽  
Order Of Magnitude ◽  
Enol Esters ◽  
The One ◽  
Neutral Conditions

<p>The monoalkylation of N-methoxypyridinium salts with alkyl radicals generated from alkenes (via hydroboration with catecholborane), alkyl iodides (via iodine atom transfer) and xanthates is reported. The reaction proceeds under neutral conditions since no acid is needed to activate the heterocycle and does not require the use of an external oxidant. A rate constant for the addition of a primary radical to N-methoxylepidinium >107 M–1 s–1 was experimentally determined. This rate constant is more than one order of magnitude larger than the one measured for the addition of primary alkyl radical to protonated lepidine demonstrating the remarkable reactivity of methoxypyridinium salts towards radicals. The reaction could be extended to a three component carbopyridinylation of electron rich alkenes including enol esters, enol ethers and enamides.</p>

On indium(III) chloride-catalyzed aldol reactions of silyl enol ethers with aldehydes in water

1998 ◽  
Vol 39 (12) ◽  
pp. 1579-1582 ◽  
Author(s):  
Shū Kobayashi ◽  
Tsuyoshi Busujima ◽  
Satoshi Nagayama
Keyword(s):  
Aldol Reactions ◽  
Enol Ethers ◽  
Silyl Enol Ethers

Enol esters XVI: Enol ethers in synthesis

1972 ◽  
Vol 49 (6) ◽  
pp. 376-377 ◽  
Author(s):  
Edward S. Rothman ◽  
Gordon G. Moore ◽  
John M. Chirinko ◽  
S. Serota
Keyword(s):  
Enol Ethers ◽  
Enol Esters
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