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Diastereoselective Mannich reactions of pseudo-C₂-symmetric glutarimide with activated imines

Tatsuya Ishikawa, Tomoko Kawasaki-Takasuka, Toshio Kubota and Takashi Yamazaki

Beilstein J. Org. Chem. 2017, 13, 2473–2477. https://doi.org/10.3762/bjoc.13.244

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Diastereoselective Mannich reactions of pseudo-C₂-symmetric glutarimide with activated imines

Tatsuya Ishikawa, Tomoko Kawasaki-Takasuka, Toshio Kubota and Takashi Yamazaki

Beilstein J. Org. Chem. 2017, 13, 2473–2477. https://doi.org/10.3762/bjoc.13.244

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Ishikawa, T.; Kawasaki-Takasuka, T.; Kubota, T.; Yamazaki, T. Beilstein J. Org. Chem. 2017, 13, 2473–2477. doi:10.3762/bjoc.13.244

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TY  - JOUR
A1  - Ishikawa, Tatsuya
A1  - Kawasaki-Takasuka, Tomoko
A1  - Kubota, Toshio
A1  - Yamazaki, Takashi
T1  - Diastereoselective Mannich reactions of pseudo-C2-symmetric glutarimide with activated imines
JF  - Beilstein Journal of Organic Chemistry
PY  - 2017///
VL  - 13
SP  - 2473
EP  - 2477
SN  - 1860-5397
DO  - 10.3762/bjoc.13.244
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.13.244
KW  - chiral oxazolidinones
KW  - diastereoselectivity
KW  - Mannich reactions
KW  - pseudo-C2 symmetry
KW  - trifluoromethyl
N2  - As an extension of the boron enolate-based aldol reactions, the oxazolidinone-installed bisimide 1a from 3-(trifluoromethyl)glutaric acid was employed for Mannich reactions with tosylated imines 2 as electrophiles to successfully obtain the corresponding adducts in a stereoselective manner.
ER  -

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Scholarly Works

Październiok‐Holewa, A.; Stecko, S. doi:10.1002/9783527834204.ch3
Dabiri, M.; Lehi, N. F.; Mohammadian, R. Catalytic stereoselective Mannich-type reactions for construction of fluorinated compounds. Molecular diversity 2021, 26, 1–44. doi:10.1007/s11030-021-10235-1
Inoue, Y.; Hatayama, T.; Kawasaki-Takasuka, T.; Agou, T.; Kubota, T.; Yamazaki, T. Stereoselective aldol reactions using pseudo C2 symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione. Chemical communications (Cambridge, England) 2018, 54, 9913–9916. doi:10.1039/c8cc05458d

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