Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis
Haraldur G Gudmundsson
1
,
Christian J Kuper
1
,
F. Bonnete
1
,
Felix Urbitsch
1
,
Bryony L Elbert
1
,
1
Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, U.K.
|
Publication type: Journal Article
Publication date: 2019-10-24
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31646859
Organic Chemistry
Abstract
Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Organic Letters
2 publications, 22.22%
|
|
|
Journal of Organic Chemistry
2 publications, 22.22%
|
|
|
Beilstein Journal of Organic Chemistry
1 publication, 11.11%
|
|
|
Chemistry Letters
1 publication, 11.11%
|
|
|
ACS Catalysis
1 publication, 11.11%
|
|
|
Journal of the American Chemical Society
1 publication, 11.11%
|
|
|
Russian Chemical Reviews
1 publication, 11.11%
|
|
|
1
2
|
Publishers
|
1
2
3
4
5
6
|
|
|
American Chemical Society (ACS)
6 publications, 66.67%
|
|
|
Beilstein-Institut
1 publication, 11.11%
|
|
|
Oxford University Press
1 publication, 11.11%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 11.11%
|
|
|
1
2
3
4
5
6
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
9
Total citations:
9
Citations from 2024:
2
(22.22%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Gudmundsson H. G. et al. Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 22. pp. 14868-14882.
GOST all authors (up to 50)
Copy
Gudmundsson H. G., Kuper C. J., Bonnete F., Urbitsch F., Elbert B. L., ANDERSON E. Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 22. pp. 14868-14882.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.9b01664
UR - https://doi.org/10.1021/acs.joc.9b01664
TI - Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis
T2 - Journal of Organic Chemistry
AU - Gudmundsson, Haraldur G
AU - Kuper, Christian J
AU - Bonnete, F.
AU - Urbitsch, Felix
AU - Elbert, Bryony L
AU - ANDERSON, EDWARD F.
PY - 2019
DA - 2019/10/24
PB - American Chemical Society (ACS)
SP - 14868-14882
IS - 22
VL - 84
PMID - 31646859
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Gudmundsson,
author = {Haraldur G Gudmundsson and Christian J Kuper and F. Bonnete and Felix Urbitsch and Bryony L Elbert and EDWARD F. ANDERSON},
title = {Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.9b01664},
number = {22},
pages = {14868--14882},
doi = {10.1021/acs.joc.9b01664}
}
Cite this
MLA
Copy
Gudmundsson, Haraldur G., et al. “Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis.” Journal of Organic Chemistry, vol. 84, no. 22, Oct. 2019, pp. 14868-14882. https://doi.org/10.1021/acs.joc.9b01664.