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Literature DB >> 22486921

Enantioselective activation of stable carboxylate esters as enolate equivalents via N-heterocyclic carbene catalysts.

Lin Hao¹, Yu Du, Hui Lv, Xingkuan Chen, Huishen Jiang, Yaling Shao, Yonggui Robin Chi.

Abstract

The first N-Heterocyclic Carbene (NHC) mediated activation of stable carboxylate esters to generate enolate intermediates is disclosed. The catalytically generated arylacetic ester enolates undergo enantioselective reactions with α,β-unsaturated imines.

Entities: Chemical Disease

Mesh：

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Year: 2012 PMID： 22486921 DOI： 10.1021/ol300676w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

25 in total

1. Carbene catalysis: An internal affair.

Authors: Jeffrey W Bode
Journal: Nat Chem Date: 2013-10 Impact factor: 24.427

Review 2. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors: Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal: Chem Rev Date: 2015-05-20 Impact factor: 60.622

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

4. β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis.

Authors: Zhenqian Fu; Jianfeng Xu; Tingshun Zhu; Wendy Wen Yi Leong; Yonggui Robin Chi
Journal: Nat Chem Date: 2013-07-21 Impact factor: 24.427

5. A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.

Authors: Javier Izquierdo; Ane Orue; Karl A Scheidt
Journal: J Am Chem Soc Date: 2013-07-11 Impact factor: 15.419

Review 6. Acyclic Twisted Amides.

Authors: Guangrong Meng; Jin Zhang; Michal Szostak
Journal: Chem Rev Date: 2021-08-18 Impact factor: 72.087

Enantioselective activation of stable carboxylate esters as enolate equivalents via N-heterocyclic carbene catalysts.

1. Carbene catalysis: An internal affair.

Review 2. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

4. β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis.

5. A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.

Review 6. Acyclic Twisted Amides.

7. Single-electron Carbene Catalysis in Redox Processes.

8. N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

9. S_NAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

10. NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.