English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  The Catalytic Asymmetric Intermolecular Prins Reaction

Díaz-Oviedo, C. D., Maji, R., & List, B. (2021). The Catalytic Asymmetric Intermolecular Prins Reaction. Journal of the American Chemical Society, 143(49), 20598-20604. doi:10.1021/jacs.1c10245.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files
hide Files
:
Diaz-Oviedo-Maji-List.pdf (Publisher version), 2MB
Name:
Diaz-Oviedo-Maji-List.pdf
Description:
-
Visibility:
Public
MIME-Type / Checksum:
application/pdf / [MD5]
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Díaz-Oviedo, C. David1, Author              
Maji, Rajat1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

Content

show
hide
Free keywords: -
 Abstract: Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Brønsted acid catalysts. Isotope labeling experiments and computations suggest a concerted, highly asynchronous addition of an acid-activated formaldehyde oligomer to the olefin. The enantioenriched 1,3-dioxanes can be transformed into the corresponding optically active 1,3-diols, which are valuable synthetic building blocks.

Details

show
hide
Language(s): eng - English
 Dates: 2021-09-272021-11-302021-12-15
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.1c10245
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 143 (49) Sequence Number: - Start / End Page: 20598 - 20604 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870