CpRuII-chiral bisamidine complex catalyzed asymmetric Carroll-type decarboxylative allylation of β-keto allyl esters

Tetrahedron ◽  
2020 ◽  
Vol 76 (7) ◽  
pp. 130888 ◽  
Author(s):  
Shintarou Ogawa ◽  
Kengo Miyata ◽  
Sho Kawakami ◽  
Shinji Tanaka ◽  
Masato Kitamura
Keyword(s):  
Decarboxylative Allylation ◽  
Allyl Esters

scholarly journals Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guogang Deng ◽  
Shengzu Duan ◽  
Jing Wang ◽  
Zhuo Chen ◽  
Tongqi Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allyl Ether ◽  
Metal Catalyst ◽  
Metal Free ◽  
Allyl Ethers ◽  
Bond Forming ◽  
Allyl Halides ◽  
Synthetic Utility ◽  
Insight Into ◽  
Allyl Esters

AbstractAllylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

Reactivity of α-trifluoromethanesulfonyl esters, amides and ketones: Decarboxylative allylation, methylation, and enol formation

2013 ◽  
Vol 153 ◽  
pp. 151-161 ◽  
Author(s):  
Han Il Kong ◽  
Monica A. Gill ◽  
Amy H. Hrdina ◽  
Jennifer E. Crichton ◽  
Jeffrey M. Manthorpe
Keyword(s):  
Decarboxylative Allylation ◽  
Enol Formation

Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

RSC Advances ◽  
2016 ◽  
Vol 6 (88) ◽  
pp. 85058-85062 ◽  
Author(s):  
Mayaka Maeno ◽  
Hiroya Kondo ◽  
Etsuko Tokunaga ◽  
Norio Shibata
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Asymmetric Synthesis ◽  
Therapeutic Agent ◽  
The Self ◽  
Keto Ester ◽  
Catalytic Asymmetric Synthesis ◽  
Palladium Catalyzed ◽  
Catalytic Asymmetric ◽  
Decarboxylative Allylation

Catalytic asymmetric synthesis of fluorinated donepezil, a promising new therapeutic agent for Alzheimer's disease, was achieved.

Enantioselective Allylations of Azlactones with Unsymmetrical Acyclic Allyl Esters

1999 ◽  
Vol 121 (46) ◽  
pp. 10727-10737 ◽  
Author(s):  
Barry M. Trost ◽  
Xavier Ariza
Keyword(s):  
Allyl Esters

Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction of γ,δ-unsaturated ketones

2015 ◽  
Vol 51 (57) ◽  
pp. 11512-11514 ◽  
Author(s):  
Shu-Jie Chen ◽  
Guo-Ping Lu ◽  
Chun Cai
Keyword(s):  
Allylic Alcohols ◽  
Unsaturated Ketones ◽  
Efficient Construction ◽  
Decarboxylative Allylation

A highly regioselective protocol is reported for the efficient construction of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols.

Enantioenriched Allyl Esters via Lipase-Vanadium Combo Catalysis

Synfacts ◽  
2011 ◽  
Vol 2011 (02) ◽  
pp. 0168-0168
Author(s):  
S. Akai ◽  
R. Hanada ◽  
N. Fujiwara ◽  
Y. Kita ◽  
M. Egi
Keyword(s):  
Allyl Esters
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