글로벌 연구동향
분자영상 및 방사화학
- 2017년 03월호
[Angew Chem Int Ed Engl.] Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers.성균관대/ 심재훈, 송충의*
- 출처
- Angew Chem Int Ed Engl.
- 등재일
- 2017 Feb 6
- 저널이슈번호
- 56(7):1835-1839. doi: 10.1002/anie.201611466. Epub 2017 Jan 18.
- 내용
Abstract
Water enables new catalytic reactions for otherwise unreactive substrate systems. Under the "on water" reaction conditions, extremely unreactive β,β-disubstituted nitroalkenes smoothly underwent enantioselective Michael addition reactions with dithiomalonates using a chiral squaramide catalyst, affording both enantiomers of highly enantioenriched Michael adducts with all-carbon-substituted quaternary centers. The developed "on water" protocol was successfully applied for the scalable one-pot syntheses of chiral GABA analogs with all-carbon quaternary stereogenic centers at the β-position, which might show highly interesting pharmaceutical properties.
Author information
Sim JH1, Song CE1.
1Department of Chemistry, Sungkyunkwan University, Suwon, 440-746, Korea.
- 키워드
- Michael addition; amino acids; asymmetric organocatalysis; stereogenic centers; water
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