Effective Activation of Carbonyl and Related Compounds with Phosphonium Salts. The Aldol and Michael Reactions of Carbonyl Compounds with Silyl Nucleophiles and Alkyl Enol Ethers

1989 ◽  
Vol 18 (6) ◽  
pp. 993-996 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Shigekazu Matsui ◽  
Kouichi Kashiwagi
Keyword(s):  
Carbonyl Compounds ◽  
Phosphonium Salts ◽  
Effective Activation ◽  
Enol Ethers ◽  
Michael Reactions ◽  
Alkyl Enol Ethers ◽  
Related Compounds

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

Low-Temperature Syntheses of Thioketals from Enol Ethers and Carbonyl Compounds.

ChemInform ◽  
2003 ◽  
Vol 34 (19) ◽  
Author(s):  
Arnaud Martel ◽  
Sopa Chewchanwuttiwong ◽  
Gilles Dujardin ◽  
Eric Brown
Keyword(s):  
Low Temperature ◽  
Carbonyl Compounds ◽  
Enol Ethers
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