Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates
2
Process Chemistry Development, Takeda Pharmaceuticals International Co., Cambridge, Massachusetts 02139, United States
|
Publication type: Journal Article
Publication date: 2019-12-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31833780
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We report a new catalytic method for alcohol sulfamoylation that deploys electron-deficient aryl sulfamates as activated group transfer reagents. The reaction utilizes the simple organic base N-methylimidazole, proceeds under mild conditions, and provides intrinsic selectivity for 1° over 2° alcohols (up to >40:1 for certain nucleosides). The requisite aryl sulfamate donors are stable crystalline solids that can be readily prepared on a large scale. Mechanistic considerations support the intermediacy of HNSO2 "aza-sulfene" in the transfer reaction.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
6
|
|
|
Organic Letters
6 publications, 37.5%
|
|
|
Chemical Science
2 publications, 12.5%
|
|
|
Molecules
1 publication, 6.25%
|
|
|
Physical Chemistry Chemical Physics
1 publication, 6.25%
|
|
|
Journal of the American Chemical Society
1 publication, 6.25%
|
|
|
Organic Reaction Mechanisms
1 publication, 6.25%
|
|
|
Journal of Organic Chemistry
1 publication, 6.25%
|
|
|
Synthesis
1 publication, 6.25%
|
|
|
1
2
3
4
5
6
|
Publishers
|
1
2
3
4
5
6
7
8
|
|
|
American Chemical Society (ACS)
8 publications, 50%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 18.75%
|
|
|
Wiley
3 publications, 18.75%
|
|
|
MDPI
1 publication, 6.25%
|
|
|
Georg Thieme Verlag KG
1 publication, 6.25%
|
|
|
1
2
3
4
5
6
7
8
|
- 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
16
Total citations:
16
Citations from 2024:
8
(50%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Rapp P. B. et al. Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates // Organic Letters. 2019. Vol. 22. No. 1. pp. 168-174.
GOST all authors (up to 50)
Copy
Rapp P. B., MURAI K., Ichiishi N., Leahy D. E., Miller S. J. Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates // Organic Letters. 2019. Vol. 22. No. 1. pp. 168-174.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b04119
UR - https://doi.org/10.1021/acs.orglett.9b04119
TI - Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates
T2 - Organic Letters
AU - Rapp, Peter B
AU - MURAI, Koichi
AU - Ichiishi, Naoko
AU - Leahy, David E.
AU - Miller, Scott J
PY - 2019
DA - 2019/12/13
PB - American Chemical Society (ACS)
SP - 168-174
IS - 1
VL - 22
PMID - 31833780
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Rapp,
author = {Peter B Rapp and Koichi MURAI and Naoko Ichiishi and David E. Leahy and Scott J Miller},
title = {Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates},
journal = {Organic Letters},
year = {2019},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.9b04119},
number = {1},
pages = {168--174},
doi = {10.1021/acs.orglett.9b04119}
}
Cite this
MLA
Copy
Rapp, Peter B., et al. “Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates.” Organic Letters, vol. 22, no. 1, Dec. 2019, pp. 168-174. https://doi.org/10.1021/acs.orglett.9b04119.