Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution
Taiga Yurino
1
,
Ryo Nishihara
2
,
Toshihisa Yasuda
3
,
Shuangli Yang
2
,
Noriyuki Utsumi
3
,
Takeaki Katayama
3
,
Noriyoshi ARAI
1
,
Takeshi Ohkuma
1
3
Central Research Laboratory, Technology and Development Division, Kanto Chemical Co. Inc, Soka, Saitama 340-0003, Japan
|
Publication type: Journal Article
Publication date: 2024-01-11
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
38205776
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Asymmetric hydrogenation of α-alkyl-substituted β-keto esters and amides with the DIPSkewphos/3-AMIQ–Ru(II) catalyst system through dynamic kinetic resolution was examined. A series of β-keto esters and amides with a simple or functionalized α-alkyl group were applicable to this reaction, affording the α-substituted β-hydroxy esters and amides in ≥99% ee (anti/syn ≥ 99:1) in many cases. The 5 g scale reaction was readily achieved. The mode of enantio- and diastereoselection in the transition state model was proposed.
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Total citations:
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Citations from 2025:
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(50%)
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Yurino T. et al. Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution // Organic Letters. 2024. Vol. 26. No. 14. pp. 2872-2876.
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Yurino T., Nishihara R., Yasuda T., Yang S., Utsumi N., Katayama T., ARAI N., Ohkuma T. Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution // Organic Letters. 2024. Vol. 26. No. 14. pp. 2872-2876.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.3c04036
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c04036
TI - Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution
T2 - Organic Letters
AU - Yurino, Taiga
AU - Nishihara, Ryo
AU - Yasuda, Toshihisa
AU - Yang, Shuangli
AU - Utsumi, Noriyuki
AU - Katayama, Takeaki
AU - ARAI, Noriyoshi
AU - Ohkuma, Takeshi
PY - 2024
DA - 2024/01/11
PB - American Chemical Society (ACS)
SP - 2872-2876
IS - 14
VL - 26
PMID - 38205776
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Yurino,
author = {Taiga Yurino and Ryo Nishihara and Toshihisa Yasuda and Shuangli Yang and Noriyuki Utsumi and Takeaki Katayama and Noriyoshi ARAI and Takeshi Ohkuma},
title = {Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c04036},
number = {14},
pages = {2872--2876},
doi = {10.1021/acs.orglett.3c04036}
}
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MLA
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Yurino, Taiga, et al. “Asymmetric Hydrogenation of α-Alkyl-Substituted β-Keto Esters and Amides through Dynamic Kinetic Resolution.” Organic Letters, vol. 26, no. 14, Jan. 2024, pp. 2872-2876. https://pubs.acs.org/doi/10.1021/acs.orglett.3c04036.