藉由碳酸銫促進掌性N-亞磺醯醛亞胺之氫磷酸酯化反應不對稱合成α,β-二胺基磷酸酯;Asymmetric Synthesis of α,β-Diamino Phosphonates from Chiral N-Sulfinyl Imine via Cs2CO3-Mediated Hydrophophonylation

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题名:	藉由碳酸銫促進掌性N-亞磺醯醛亞胺之氫磷酸酯化反應不對稱合成α,β-二胺基磷酸酯;Asymmetric Synthesis of α,β-Diamino Phosphonates from Chiral N-Sulfinyl Imine via Cs2CO3-Mediated Hydrophophonylation
作者:	游日淞;Yu, Jih-Sung
贡献者:	化學學系
关键词:	α-胺基酸;α,β-二胺基磷酸酯;(R)-(+)-叔丁基亞磺醯胺;普多維克反應;α-amino acids;α,β-diamino phosphonates;(R)-(+)-tert-butanesulfinamide;Pudovik reaction
日期:	2025-08-16
上传时间:	2025-10-17 11:35:23 (UTC+8)
出版者:	國立中央大學
摘要:	α,β-二胺基酸因其具有兩個相鄰的掌性中心結構，廣泛存在於藥物與天然物的骨架中，並且受到合成化學家的深入研究。然而，其生物電子等排體—α,β-二胺基磷酸酯，卻鮮少被探討。儘管α,β-二胺基磷酸酯在藥物開發中展現出更高的研究潛力，但受到現行有限的合成方法所限制，使得化學家難以建構出多樣化的α,β-二胺基磷酸酯。本研究利用市售胺基酸與容易取得的掌性輔助劑—(R)-(+)-叔丁基亞磺醯胺，合成一系列N-亞磺醯醛亞胺，並在碳酸銫的促進下進行不對稱普多維克反應，於溫和條件下成功合成出數十種具有不同取代基的α,β-二胺基磷酸酯。此方法不僅克服了以往在合成此類化合物時所面臨的挑戰，並創造一種操作簡便且具高原子經濟性的合成策略，為相關分子的合成提供新的路徑。 ;α,β-Diamino acids, due to their structure containing two adjacent chiral centers, are commonly found in the frameworks of pharmaceuticals and natural products and have been extensively studied by synthetic chemists. However, their bioisosteric counterparts—α,β-diamino phosphonates—have received far less attention. Despite the fact that α,β-diamino phosphonates demonstrate even greater potential in drug development, their structural diversity has been limited by the scarcity of efficient synthetic methods, posing a significant challenge for chemists aiming to access these compounds. In this study, a series of N-sulfonyl imines were synthesized using commercially available amino acids and an easily accessible chiral auxiliary—(R)-(+)-tert-butanesulfinamide. These imines underwent asymmetric Pudovik reactions promoted by cesium carbonate, enabling the successful synthesis of dozens of α,β-diaminophosphonates with various substituents under mild conditions. This method not only overcomes the challenges traditionally associated with the synthesis of such compounds, but also offers a user-friendly and atom-economical synthetic strategy, providing a new pathway for the construction of related molecules.
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