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Literature DB >> 26016987

Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN 2' Reaction.

Yusuke Kuroda¹, Shingo Harada¹, Akinori Oonishi¹, Yousuke Yamaoka¹, Ken-Ichi Yamada², Kiyosei Takasu³.

Abstract

A Brønsted-acid-catalyzed intramolecular enantioselective SN 2' reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.

Entities: Chemical

Keywords: asymmetric catalysis; nucleophilic substitution; organocatalysis; pyrrolidines

Mesh：

Substances：

Year: 2015 PMID： 26016987 DOI： 10.1002/anie.201502831

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

5 in total

1. Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

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Journal: J Org Chem Date: 2016-08-10 Impact factor: 4.354

2. Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.

Authors: Cheng-Che Tsai; Christopher Sandford; Tao Wu; Buyun Chen; Matthew S Sigman; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2020-06-30 Impact factor: 15.336

3. Molecular insights into chirality transfer from double axially chiral phosphoric acid in a synergistic enantioselective intramolecular amination.

Authors: Soumi Tribedi; Raghavan B Sunoj
Journal: Chem Sci Date: 2021-12-29 Impact factor: 9.825

4. Kinetic resolution of racemic tertiary allylic alcohols through S_N2' reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system.

Authors: Satavisha Kayal; Jun Kikuchi; Naoya Shinagawa; Shigenobu Umemiya; Masahiro Terada
Journal: Chem Sci Date: 2022-07-20 Impact factor: 9.969

5. Chiral Brønsted acid-catalyzed intramolecular S_N2' reaction for enantioselective construction of a quaternary stereogenic center.

Authors: Masahiro Shimizu; Jun Kikuchi; Azusa Kondoh; Masahiro Terada
Journal: Chem Sci Date: 2018-06-05 Impact factor: 9.825