N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

2016 ◽  
Vol 14 (4) ◽  
pp. 1485-1491 ◽  
Author(s):  
Ling Zhu ◽  
Chenxia Yu ◽  
Tuanjie Li ◽  
Yuhong Wang ◽  
Yinan Lu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acids ◽  
Spirocyclic Oxindole

An NHC-catalyzed asymmetric [4 + 2] annulation of isatins and α,β-unsaturated carboxylic acids bearing γ-H gave spirocyclic oxindole–dihydropyranones successfully via an in situ activation strategy.

N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β-Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives

2014 ◽  
Vol 126 (43) ◽  
pp. 11795-11799 ◽  
Author(s):  
Xiang-Yu Chen ◽  
Zhong-Hua Gao ◽  
Chun-Yu Song ◽  
Chun-Lin Zhang ◽  
Zhi-Xiang Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Enantioselective Synthesis ◽  
Unsaturated Carboxylic Acids

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2907-2912 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Satoshi Minakata ◽  
Kenta Takemoto ◽  
Shunsuke Yahata ◽  
Takumi Kojima
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Present Method ◽  
Medicinal Chemistry ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
Unsaturated Carboxylic Acids

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

An Enantioselective Assembly of Dihydropyranones through an NHC/LiCl-Mediated in situ Activation of α,β-Unsaturated Carboxylic Acids

2016 ◽  
Vol 11 (5) ◽  
pp. 678-681 ◽  
Author(s):  
Yonglei Que ◽  
Yinan Lu ◽  
Wenjing Wang ◽  
Yuhong Wang ◽  
Haotian Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
In Situ Activation ◽  
Unsaturated Carboxylic Acids
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