Lewis acid assisted annelation of trimethylsilyl enol ethers of 1-acetylcyclohexenes with α,β-unsaturated carbonyl compounds to give substituted 2-decalones; synthesis of (±)-ε-cadinene

1987 ◽  
pp. 1333-1335 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Akihiro Okano ◽  
Tsutomu Akama ◽  
Hisashi Uda
Keyword(s):  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Enol Ethers

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

ChemInform Abstract: Lewis-Acid-Induced Reactions of α-Methoxyglycinamide Derivatives with Silyl Enol Ethers. Formation of 3-Amino-2-pyrrolidinones and 3- Amino-2-pyrrolinones.

ChemInform ◽  
2010 ◽  
Vol 23 (48) ◽  
pp. no-no
Author(s):  
E. C. ROOS ◽  
H. HIEMSTRA ◽  
W. N. SPECKAMP ◽  
B. KAPTEIN ◽  
J. KAMPHUIS ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Enol Ethers ◽  
Silyl Enol Ethers

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

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