Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/161337
Title: Construction of tetrasubstituted silicon-stereogenic silanes via conformational isomerization and N‑heterocyclic carbenecatalyzed desymmetrization
Authors: Zhou, Mali
Liu, Jianjian
Deng, Rui
Wang, Qingyun
Wu, Shuquan
Zheng, Pengcheng
Chi, Robin Yonggui
Keywords: Science::Chemistry
Issue Date: 2022
Source: Zhou, M., Liu, J., Deng, R., Wang, Q., Wu, S., Zheng, P. & Chi, R. Y. (2022). Construction of tetrasubstituted silicon-stereogenic silanes via conformational isomerization and N‑heterocyclic carbenecatalyzed desymmetrization. ACS Catalysis, 12(13), 7781-7788. https://dx.doi.org/10.1021/acscatal.2c01082
Project: NRF-NRFI2016-06
NRF-CRP22-2019-0002
RG7/20
RG5/19
MOE2019-T2-2-117
MOE2018-T3-1-003
Journal: ACS Catalysis
Abstract: Disclosed here is a catalytic strategy for asymmetric access to chiral tetrasubstituted silicon-stereogenic silanes. Our reaction starts with a (covalently) symmetric silane bearing two aldehyde moieties as the substrate. Single-crystal structural analysis shows that the substrate exists as a racemate of two conformational enantiomers because of the presence of a Si/O weak interaction. Mechanistic studies assisted by DFT calculation indicate that the two conformational enantiomers can readily isomerize to each other, and one of the conformational enantiomers of the substrate is favorably activated by a N-heterocyclic carbene catalyst via an overall desymmetrization process to eventually afford optically enriched tetrasubstituted silicon-stereogenic silanes as the products. Our chiral silanes' products can be readily transformed to a diverse set of silicon stereogenic functional molecules.
URI: https://hdl.handle.net/10356/161337
ISSN: 2155-5435
DOI: 10.1021/acscatal.2c01082
Schools: School of Physical and Mathematical Sciences 
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.2c01082.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

SCOPUSTM   
Citations 20

18
Updated on Mar 25, 2024

Page view(s)

142
Updated on Mar 28, 2024

Download(s)

8
Updated on Mar 28, 2024

Google ScholarTM

Check

Altmetric


Plumx

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