Open Access
α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes
2
Department of Chemistry and Biochemistry
4
Auburn
5
Usa
|
Publication type: Journal Article
Publication date: 2019-06-28
scimago Q1
wos Q1
SJR: 2.138
CiteScore: 12.6
Impact factor: 7.4
ISSN: 20416520, 20416539
PubMed ID:
31489170
General Chemistry
Abstract
Cu-catalyzed stereoselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols from 1,3-dienylsilane was developed. Mechanistic studies revealed that the borocupration of dienylsilane proceeded through a 1,2-addition pathway to give an allylcopper intermediate with Cu distal to the silyl group. However, the subsequent aldehyde allylation proceeded via Curtin–Hammett control to give (E)-δ-silyl-anti-homoallylic alcohols with high diastereoselectivities. This method was applied to the synthesis of the C1–9 fragment of a polyketide natural product, mycinolide IV.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
2
4
6
8
10
12
|
|
|
Organic Letters
11 publications, 21.15%
|
|
|
Angewandte Chemie - International Edition
10 publications, 19.23%
|
|
|
Angewandte Chemie
10 publications, 19.23%
|
|
|
ACS Catalysis
4 publications, 7.69%
|
|
|
Journal of the American Chemical Society
3 publications, 5.77%
|
|
|
Journal of Organic Chemistry
3 publications, 5.77%
|
|
|
Chemical Science
3 publications, 5.77%
|
|
|
Chemical Communications
3 publications, 5.77%
|
|
|
Asian Journal of Organic Chemistry
1 publication, 1.92%
|
|
|
Chemical Reviews
1 publication, 1.92%
|
|
|
Organic Chemistry Frontiers
1 publication, 1.92%
|
|
|
Russian Chemical Reviews
1 publication, 1.92%
|
|
|
Coordination Chemistry Reviews
1 publication, 1.92%
|
|
|
2
4
6
8
10
12
|
Publishers
|
5
10
15
20
25
|
|
|
American Chemical Society (ACS)
22 publications, 42.31%
|
|
|
Wiley
21 publications, 40.38%
|
|
|
Royal Society of Chemistry (RSC)
7 publications, 13.46%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 1.92%
|
|
|
Elsevier
1 publication, 1.92%
|
|
|
5
10
15
20
25
|
- 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
52
Total citations:
52
Citations from 2024:
12
(23.07%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Gao S. et al. α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes // Chemical Science. 2019. Vol. 10. No. 32. pp. 7554-7560.
GOST all authors (up to 50)
Copy
Gao S., Chen M. α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes // Chemical Science. 2019. Vol. 10. No. 32. pp. 7554-7560.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/c9sc02905b
UR - https://xlink.rsc.org/?DOI=C9SC02905B
TI - α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes
T2 - Chemical Science
AU - Gao, Shang
AU - Chen, Ming
PY - 2019
DA - 2019/06/28
PB - Royal Society of Chemistry (RSC)
SP - 7554-7560
IS - 32
VL - 10
PMID - 31489170
SN - 2041-6520
SN - 2041-6539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Gao,
author = {Shang Gao and Ming Chen},
title = {α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes},
journal = {Chemical Science},
year = {2019},
volume = {10},
publisher = {Royal Society of Chemistry (RSC)},
month = {jun},
url = {https://xlink.rsc.org/?DOI=C9SC02905B},
number = {32},
pages = {7554--7560},
doi = {10.1039/c9sc02905b}
}
Cite this
MLA
Copy
Gao, Shang, et al. “α-Silicon effect assisted Curtin–Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.” Chemical Science, vol. 10, no. 32, Jun. 2019, pp. 7554-7560. https://xlink.rsc.org/?DOI=C9SC02905B.