Total synthesis of (−)-aplaminal by Buchwald–Hartwig cross-coupling of an aminal

Ohyoshi, Takayuki; Akemoto, Kei; Taniguchi, Ayaka; Ishihara, Takuma; Kigoshi, Hideo

doi:10.1039/c9nj04743c

Cited by 4 publications

(2 citation statements)

References 15 publications

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“…Therefore, the ultimate way to evaluate the influence of all these variables is applying this knowledge to the arduous field of total synthesis. We selected a few examples of natural product containing the aminal framework within their structures [131][132][133][134][135][136][137][138][139][140][141][142][143][144][145][146][147][148] (Scheme 31) considering the following aspects of their respective synthesis: a) pathway for aminal formation, b) synthetic step which the aminal was formed and, when applicable, c) conditions used thereafter. When analyzing the first two variables we can see that, contrasting with the myriad of synthetic methods available for the construction of simpler aminal systems, the synthesis of aminals in the field of total synthesis is much more limited.…”

Section: Synthesis Of Aminal-containing Natural Productsmentioning

confidence: 99%

“…framework within their structures, 73,[131][132][133][134][135][136][137][138][139][140][141][142][143][144][145][146][147][148] and consider the following aspects of their respective syntheses: (a) the pathway for aminal formation, (b) the synthetic step during which the aminal is formed, and, when applicable, (c) the conditions used thereafter (Figure 1). When analyzing the first two variables we can see that, contrasting with the myriad of synthetic methods available for the construction of simpler aminal systems, the synthesis of aminals in the field of total synthesis is much more limited.…”

Section: Review Synthesismentioning

confidence: 99%

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Progress on the Synthesis and Applications of Aminals: Scaffolds for Molecular Diversity

Rippel,

Ferreira,

Branco

2024

Synthesis

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Aminals, characterized by a central carbon linking two nitrogen atoms, are versatile building blocks in modern chemistry. This review addresses a literature gap by exploring the synthesis and applications of aminals, with a focus on drug discovery and molecular diversity. Beyond medicinal chemistry, aminals find applications as key components in bioactive compounds and versatile tools in materials chemistry. The review covers fundamental characteristics, synthetic methodologies, stability, and applications, emphasizing alternative synthesis methods to the well-established aldehyde-amine condensation. This inclusive exploration provides insights into diverse synthetic pathways, expanding the versatility of the aminal scaffold. 1. Introduction 2. The Aminal Group 3. Aminal Synthesis 3.1 Metal-free Approaches 3.2 Metal-catalyzed Approaches 3.3 Photoredox Methodologies 3.4 Via rearrangements 3.5 Decarboxylative Coupling 4. Aminals as Synthetic Tools 5. Synthesis of Aminal-containing Natural Products 6. Aminal-based Materials 7. Conclusions

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