Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines
Publication type: Journal Article
Publication date: 2022-06-01
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
35649184
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An enantioselective selenocyclization of 1,1-disubstituted alkenes was achieved for the first time, which is enabled by a novel combination of a chiral BINAM-derived sulfide and an achiral Lewis acid. Various selenium-containing 4H-3,1-benzoxazines, which are widely present in a range of medicinally relevant molecules, were readily obtained in moderate to good yields and good to excellent enantioselectivities. A series of tetrasubstituted carbon stereocenters were facilely constructed.
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Metrics
33
Total citations:
33
Citations from 2025:
12
(36.36%)
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GOST
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Cao R. et al. Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines // Organic Letters. 2022. Vol. 24. No. 22. pp. 4093-4098.
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Cao R., Yu L., Huo Yu. X., Li Y., Xue X., Chen Z. M. Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines // Organic Letters. 2022. Vol. 24. No. 22. pp. 4093-4098.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c01731
UR - https://doi.org/10.1021/acs.orglett.2c01731
TI - Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines
T2 - Organic Letters
AU - Cao, Ren-Fei
AU - Yu, Lu
AU - Huo, Yu Xuan
AU - Li, Yao
AU - Xue, Xiao-Song
AU - Chen, Zhi Min
PY - 2022
DA - 2022/06/01
PB - American Chemical Society (ACS)
SP - 4093-4098
IS - 22
VL - 24
PMID - 35649184
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
Copy
@article{2022_Cao,
author = {Ren-Fei Cao and Lu Yu and Yu Xuan Huo and Yao Li and Xiao-Song Xue and Zhi Min Chen},
title = {Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.2c01731},
number = {22},
pages = {4093--4098},
doi = {10.1021/acs.orglett.2c01731}
}
Cite this
MLA
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Cao, Ren-Fei, et al. “Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines.” Organic Letters, vol. 24, no. 22, Jun. 2022, pp. 4093-4098. https://doi.org/10.1021/acs.orglett.2c01731.