English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Chiral Phosphoric Acid Catalyzed Conversion of Epoxides into Thiiranes: Mechanism, Stereochemical Model, and New Catalyst Design

Duan, M., Díaz-Oviedo, C. D., Zhou, Y., Chen, X., Yu, P., List, B., et al. (2022). Chiral Phosphoric Acid Catalyzed Conversion of Epoxides into Thiiranes: Mechanism, Stereochemical Model, and New Catalyst Design. Angewandte Chemie International Edition, 61(9): e202113204. doi:10.1002/ange.202113204.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Duan, Meng1, 2, 3, Author
Díaz-Oviedo, Christian David4, Author              
Zhou, Yang3, Author
Chen, Xiangyang2, Author
Yu , Peiyuan3, Author
List, Benjamin4, Author              
Houk, Kendall N.2, Author
Lan, Yu1, Author
Affiliations:
1Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China, ou_persistent22              
2Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095 USA, ou_persistent22              
3Department of Chemistry and Shenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China, ou_persistent22              
4Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

Content

show
hide
Free keywords: Catalyst Design; Chiral Phosphoric Acids; DFT Calculations; Organocatalysis; Stereochemical Model
 Abstract: Computations and experiments leading to new chiral phosphoric acids (CPAs) for epoxide thionations are reported. Density functional theory calculations reveal the mechanism and origin of the enantioselectivity of such CPA-catalyzed epoxide thionations. The calculated mechanistic information was used to design new efficient CPAs that were tested experimentally and found to be highly effective. Bulky ortho-substituents on the 3,3′-aryl groups of the CPA are important to restrict the position of the epoxide in the key transition states for the enantioselectivity-determining step. Larger para-substituents significantly improve the enantioselectivity of the reaction.

Details

show
hide
Language(s): eng - English
 Dates: 2021-09-292021-12-082022-02-21
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/ange.202113204
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (9) Sequence Number: e202113204 Start / End Page: - Identifier: CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851