A simple and efficient method for C‐2 deuterium labeling of 3,4‐di‐tert‐butoxypyrroline N‐oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was ...
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https://www.riss.kr/link?id=O112845524
2020년
-
1434-193X
1099-0690
SCI;SCIE;SCOPUS
학술저널
3423-3429 [※수록면이 p5 이하이면, Review, Columns, Editor's Note, Abstract 등일 경우가 있습니다.]
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
A simple and efficient method for C‐2 deuterium labeling of 3,4‐di‐tert‐butoxypyrroline N‐oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was ...
A simple and efficient method for C‐2 deuterium labeling of 3,4‐di‐tert‐butoxypyrroline N‐oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was achieved by base‐catalyzed H/D exchange in D2O under mild reaction conditions. A mechanistic pathway based on kinetic and computational data was proposed. The labeled nitrone was used in the synthesis of C‐8a deuterated (1R,2R,8aR)‐lentiginosine.
A dialkoxy five‐membered cyclic nitrone smoothly undergoes a base‐catalyzed direct H/D exchange through umpolung reactivity of the carbon atom of the nitrone moiety. Deuterium is incorporated into a useful and versatile building block with total selectivity and a high percentage. Kinetic and in silico data indicate the formation of a transient carbenoid anion.
Front Cover: Aliphatic α‐Boryl‐α‐bromoketones: Synthesis and Reactivity (Eur. J. Org. Chem. 23/2020)
Supramolecular Catalysts Featuring Crown Ethers as Recognition Units