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Updated: May 16, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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反射性キラリティ移転 (RCT):非キラル銅触媒によるα-アミノ酸シフ基の非対称1,3-二極サイクロアディション

Kazuhiro Morisaki1, Yuto Furuki1, Rento Kousaka1

  • 1Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

Journal of the American Chemical Society
|April 1, 2025
PubMed
まとめ

この研究は,既存のアミノ酸からキラルな非自然なアミノ酸を作り出すための触媒的方法を導入しています. 新しい反射性キラリティ移転 (RCT) 戦略は,合成を簡素化し,外部触媒を回避します.

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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