Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution
Chenzong Li
1, 2
,
Xun Xiang
1, 2
,
Xianghe Zhang
1
,
Zhao-Lin He
2
,
Zhao Lin He
2
,
Shuangxi Gu
2
,
Publication type: Journal Article
Publication date: 2023-02-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
36779869
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Chiral benzoxazinones and 4H-3,1-benzoxazines as important motifs are widely found in abundant pharmaceuticals and biological molecules. We herein successfully developed the first kinetic resolution (KR) process of racemic benzoxazinones through Ir-catalyzed asymmetric intramolecular allylation, furnishing a wide range of chiral benzoxazinones and 4H-3,1-benzoxazines with excellent results via outstanding KR performances (with the s factor up to 170). This protocol exhibited broad substrate scope generality and good functional group tolerance, and the chiral 4H-3,1-benzoxazine products could be readily transformed to other useful optically active heterocycles.
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7
Total citations:
7
Citations from 2025:
3
(42.86%)
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GOST
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Li C. et al. Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution // Organic Letters. 2023. Vol. 25. No. 7. pp. 1172-1177.
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Li C., Xiang X., Zhang X., He Z., He Z. L., Gu S., Dong X. Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution // Organic Letters. 2023. Vol. 25. No. 7. pp. 1172-1177.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.3c00148
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c00148
TI - Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution
T2 - Organic Letters
AU - Li, Chenzong
AU - Xiang, Xun
AU - Zhang, Xianghe
AU - He, Zhao-Lin
AU - He, Zhao Lin
AU - Gu, Shuangxi
AU - Dong, Xiu-Qin
PY - 2023
DA - 2023/02/13
PB - American Chemical Society (ACS)
SP - 1172-1177
IS - 7
VL - 25
PMID - 36779869
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2023_Li,
author = {Chenzong Li and Xun Xiang and Xianghe Zhang and Zhao-Lin He and Zhao Lin He and Shuangxi Gu and Xiu-Qin Dong},
title = {Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c00148},
number = {7},
pages = {1172--1177},
doi = {10.1021/acs.orglett.3c00148}
}
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MLA
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Li, Chenzong, et al. “Iridium-Catalyzed Intramolecular Asymmetric Allylation of Vinyl Benzoxazinones for the Synthesis of Chiral 4H-3,1-Benzoxazines via Kinetic Resolution.” Organic Letters, vol. 25, no. 7, Feb. 2023, pp. 1172-1177. https://pubs.acs.org/doi/10.1021/acs.orglett.3c00148.
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