English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
  A Catalytic Asymmetric Hydrolactonization

Maji, R., Ghosh, S., Grossmann, O., Zhang, P., Leutzsch, M., Tsuji, N., et al. (2023). A Catalytic Asymmetric Hydrolactonization. Journal of the American Chemical Society, 145(16), 8788-8793. doi:10.1021/jacs.3c01404.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Maji, Rajat1, Author           
Ghosh, Santanu1, Author           
Grossmann, Oleg1, Author           
Zhang, Pinglu1, Author           
Leutzsch, Markus2, Author           
Tsuji, Nobuya3, Author           
List, Benjamin1, 3, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              
3Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo 001-0021, Japan, ou_persistent22              

Content

show
hide
Free keywords: -
 Abstract: Despite recent advancements in the development of catalytic asymmetric electrophile induced lactonization reactions of olefinic carboxylic acids, the archetypical hydrolactonization has long remained an unsolved and well-recognized challenge. Here, we report the realization of a catalytic asymmetric hydrolactonization using a confined imidodiphosphorimidate (IDPi) Brønsted acid catalyst. The method is operationally simple, scalable, and compatible with a wide variety of substrates. Its potential is showcased with concise syntheses of the sesquiterpenes (−)-boivinianin A and (+)-gossonorol. Through in-depth physicochemical and DFT analyses, we derive a nuanced picture of the mechanism and enantioselectivity of this reaction.

Details

show
hide
Language(s): eng - English
 Dates: 2023-02-072023-04-122023-04-26
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.3c01404
 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: 145 (16) Sequence Number: - Start / End Page: 8788 - 8793 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870