scholarly journals α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers

ACS Catalysis ◽  
2020 ◽  
Vol 10 (19) ◽  
pp. 11430-11437 ◽  
Author(s):  
Jamie A. Leitch ◽  
Thomas Rossolini ◽  
Tatiana Rogova ◽  
Darren J. Dixon
Keyword(s):  
Enol Ethers ◽  
Alkyl Enol Ethers ◽  
Ether Synthesis

scholarly journals α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers

2020 ◽  
Author(s):  
Jamie Leitch ◽  
Thomas Rossolini ◽  
Tatiana Rogova ◽  
Darren J. Dixon
Keyword(s):  
Single Electron Transfer ◽  
Enol Ether ◽  
Enol Ethers ◽  
Ion Generation ◽  
Wide Range ◽  
Oxocarbenium Ion ◽  
Alkyl Enol Ethers ◽  
Ether Synthesis ◽  
Dialkyl Ethers ◽  
Led Irradiation

The photocatalytic construction of C(sp<sup>3</sup>)-rich α-tertiary dialkyl ethers through the reductive α-functionalization of alkyl enol ether substrates with conjugated alkenes in the presence of a Hantzsch ester terminal reductant under blue LED irradiation, is described. Pivoting on oxocarbenium ion generation <i>via</i> an initial TMSCl-facilitated protic activation of the enol ether substrate, subsequent single electron transfer delivers the key nucleophilic α-oxy tertiary radical capable of productively combining with a variety of alkene substrates. The new reductive functionalization strategy was simple to perform, efficient, broad in scope with respect to both alkene acceptor and enol ether donor fragments and delivered a wide range of complex α-tertiary dialkyl ether architectures.

scholarly journals α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers

2020 ◽  
Author(s):  
Jamie Leitch ◽  
Thomas Rossolini ◽  
Tatiana Rogova ◽  
Darren J. Dixon
Keyword(s):  
Single Electron Transfer ◽  
Enol Ether ◽  
Enol Ethers ◽  
Ion Generation ◽  
Wide Range ◽  
Oxocarbenium Ion ◽  
Alkyl Enol Ethers ◽  
Ether Synthesis ◽  
Dialkyl Ethers ◽  
Led Irradiation

The photocatalytic construction of C(sp<sup>3</sup>)-rich α-tertiary dialkyl ethers through the reductive α-functionalization of alkyl enol ether substrates with conjugated alkenes in the presence of a Hantzsch ester terminal reductant under blue LED irradiation, is described. Pivoting on oxocarbenium ion generation <i>via</i> an initial TMSCl-facilitated protic activation of the enol ether substrate, subsequent single electron transfer delivers the key nucleophilic α-oxy tertiary radical capable of productively combining with a variety of alkene substrates. The new reductive functionalization strategy was simple to perform, efficient, broad in scope with respect to both alkene acceptor and enol ether donor fragments and delivered a wide range of complex α-tertiary dialkyl ether architectures.

Divergent stereoselective synthesis of (E) and (Z) O-Alkyl enol ethers

1992 ◽  
Vol 33 (20) ◽  
pp. 2863-2866 ◽  
Author(s):  
Lluís Solá ◽  
Jaume Castro ◽  
Albert Moyano ◽  
Miquel A. Pericás ◽  
Antoni Riera
Keyword(s):  
Stereoselective Synthesis ◽  
Enol Ethers ◽  
Alkyl Enol Ethers

Trityl Salts Catalyzed Aldol-Type Reaction of Alkyl Enol Ethers with Acetals

1987 ◽  
Vol 16 (6) ◽  
pp. 1051-1052 ◽  
Author(s):  
Masahiro Murakami ◽  
Hiroyuki Minamikawa ◽  
Teruaki Mukaiyama
Keyword(s):  
Enol Ethers ◽  
Type Reaction ◽  
Alkyl Enol Ethers

ChemInform Abstract: Divergent Stereoselective Synthesis of E- and Z-O-Alkyl Enol Ethers.

ChemInform ◽  
2010 ◽  
Vol 23 (46) ◽  
pp. no-no
Author(s):  
L. SOLA ◽  
J. CASTRO ◽  
A. MOYANO ◽  
M. A. PERICAS ◽  
A. RIERA
Keyword(s):  
Stereoselective Synthesis ◽  
Enol Ethers ◽  
Alkyl Enol Ethers

Facile synthesis of pyrroles via Rh(II)-catalyzed transannulation of 1-tosyl-1,2,3-triazoles with silyl or alkyl enol ethers

2014 ◽  
Vol 55 (47) ◽  
pp. 6455-6458 ◽  
Author(s):  
Juan Feng ◽  
Yuanhao Wang ◽  
Qingong Li ◽  
Renwang Jiang ◽  
Yefeng Tang
Keyword(s):  
Facile Synthesis ◽  
Enol Ethers ◽  
Alkyl Enol Ethers

Facile synthesis of chiral O-alkyl enol ethers

1987 ◽  
Vol 52 (11) ◽  
pp. 2303-2306 ◽  
Author(s):  
Florence Charbonnier ◽  
Albert Moyano ◽  
Andrew E. Greene
Keyword(s):  
Facile Synthesis ◽  
Enol Ethers ◽  
Alkyl Enol Ethers
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