Efficient and Scalable Synthesis of 6,6-Dimethyl-3-oxabicyclo [3.1.0]hexan-2-one through Organocatalyzed Desymmetrization and Chemoselective Reduction,Synthesis

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Efficient and Scalable Synthesis of 6,6-Dimethyl-3-oxabicyclo [3.1.0]hexan-2-one through Organocatalyzed Desymmetrization and Chemoselective Reduction
Synthesis ( IF 2.2 ) Pub Date : 2024-01-02 , DOI: 10.1055/a-2217-0996
Guillaume Tintori ₁ , Clément Jacob ₁ , Christine Delsarte ₁ , François Potié ₁ , Laurence Grimaud ₂ , maxime Vitale ₃ , Pierre-Georges Echeverria ₁

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The development of a robust process to 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one, a key intermediate toward several active compounds of interest, is described. A scalable organocatalyzed desymmetrization was first studied and the reaction proved to be compatible with standard dilution. A kinetic study was performed to elucidate substrate and catalyst concentration dependences. Next, a chemoselective reduction of the carboxylic acid was developed. The scalability was demonstrated on 100 g scale through a fully telescoped process.

中文翻译：

通过有机催化去对称和化学选择性还原高效、可规模化合成 6,6-二甲基-3-氧杂双环 [3.1.0]己-2-酮

描述了 6,6-二甲基-3-氧杂双环[3.1.0]己-2-酮（几种感兴趣的活性化合物的关键中间体）的稳健工艺的开发。首先研究了可扩展的有机催化去对称反应，并证明该反应与标准稀释相容。进行动力学研究以阐明底物和催化剂浓度依赖性。接下来，开发了羧酸的化学选择性还原。通过完全伸缩过程在 100 g 规模上展示了可扩展性。

更新日期：2024-01-03

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