English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
  Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans

Xie, Y., Cheng, G.-J., Lee, S., Kaib, P. S. J., Thiel, W., & List, B. (2016). Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans. Journal of the American Chemical Society, 138(44), 14538-14541. doi:10.1021/jacs.6b09129.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Xie, Youwei1, Author              
Cheng, Gui-Juan2, Author              
Lee, Sunggi1, Author              
Kaib, Philip S. J.1, Author              
Thiel, Walter2, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

Content

show
hide
Free keywords: -
 Abstract: We describe the design and development of the fi rst catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an e ffi cient approach for highly diastereo- and enantioselective synthesis of tetrahydrofur- ans (THFs) and is catalyzed by a con fi ned chiral imidodiphosphoric acid (IDP). Aromatic and heteroar- omatic aldehydes react with various 3,5-dien-1-ols to a ff ord 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphor- imidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.

Details

show
hide
Language(s): eng - English
 Dates: 2016-08-312016-10-272016-11-09
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.6b09129
 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: 138 (44) Sequence Number: - Start / End Page: 14538 - 14541 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870