Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/155113
Title: Chemo-selective cross reaction of two enals via carbene-catalyzed dual activation
Authors: Peng, Xiaolin
Xu, Jun
Li, Tingting
Chi, Robin Yonggui
Jin, Zhichao
Keywords: Science::Chemistry
Issue Date: 2020
Source: Peng, X., Xu, J., Li, T., Chi, R. Y. & Jin, Z. (2020). Chemo-selective cross reaction of two enals via carbene-catalyzed dual activation. Chemical Science, 11(46), 12533-12539. https://dx.doi.org/10.1039/d0sc03297b
Project: NRF-NRFI2016-06)
RG108/16
RG5/19
RG1/18
MOE2018-T3-1-003
A1783c0008
A1783c0010
Journal: Chemical Science
Abstract: A dual catalytic chemo-selective cross-coupling reaction of two enals is developed. One enal (without α-substitution) is activated by an NHC catalyst to form an acylazolium enolate intermediate that undergoes Michael-type addition to another enal molecule bearing an alkynyl substituent. Mechanistic studies indicate that non-covalent interactions between the alkynyl enal and the NHC·HX catalyst play important roles in substrate activation and enantioselectivity control. Many of the possible side reactions are not observed. Our reaction provides highly chemo- and diastereo-selective access to chiral lactones containing functionalizable 1,3-enyn units with excellent enantioselectivities (95 to >99% ee).
URI: https://hdl.handle.net/10356/155113
ISSN: 2041-6520
DOI: 10.1039/d0sc03297b
Rights: © 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

Files in This Item:
File Description SizeFormat 
Chemo-selective cross reaction of two enals via carbene-catalyzed dual activation.pdf2.02 MBAdobe PDFView/Open

Page view(s)

20
Updated on May 19, 2022

Download(s)

4
Updated on May 19, 2022

Google ScholarTM

Check

Altmetric


Plumx

Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.