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Organocatalytic Asymmetric Cascade Reaction between o‐Hydroxycinnamaldehydes and γ/δ‐Hydroxyenones: A Route to Tetrahydrofuran/Tetrahydropyran‐Fused 3,4‐Dihydrocoumarins
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-10-12 , DOI: 10.1002/adsc.201800900 Buddhadeb Mondal 1 , Subhas Chandra Pan 1
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-10-12 , DOI: 10.1002/adsc.201800900 Buddhadeb Mondal 1 , Subhas Chandra Pan 1
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The first organocatalytic asymmetric synthesis of tetrahydrofuran/tetrahydropyran‐fused 3,4‐dihydrocoumarin has been developed via a cascade reaction between 2‐hydroxy cinnamaldehydes and γ/δ‐hydroxy enones followed by pyridinium chlorochromate oxidation. Diphenylprolinol silyl ether catalyst in combination with acetic acid was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst and the additive, the desired products were obtained in high enantio‐ and diastereoselectivities.
中文翻译:
邻羟基肉桂醛与γ/δ羟基烯酮之间的有机催化不对称级联反应:一条通往四氢呋喃/四氢吡喃融合的3,4-二氢香豆素的途径
通过2-羟基肉桂醛和γ / δ-羟基烯酮的级联反应,然后进行吡啶鎓氯代铬酸铬的氧化,开发了第一个有机催化不对称合成四氢呋喃/四氢吡喃稠合的3,4-二氢香豆素。发现二苯基脯氨醇甲硅烷基醚催化剂与乙酸结合对于级联反应是最有效的。用10摩尔%的催化剂和添加剂,可以得到高对映选择性和非对映选择性的所需产物。
更新日期:2018-10-12
中文翻译:
邻羟基肉桂醛与γ/δ羟基烯酮之间的有机催化不对称级联反应:一条通往四氢呋喃/四氢吡喃融合的3,4-二氢香豆素的途径
通过2-羟基肉桂醛和γ / δ-羟基烯酮的级联反应,然后进行吡啶鎓氯代铬酸铬的氧化,开发了第一个有机催化不对称合成四氢呋喃/四氢吡喃稠合的3,4-二氢香豆素。发现二苯基脯氨醇甲硅烷基醚催化剂与乙酸结合对于级联反应是最有效的。用10摩尔%的催化剂和添加剂,可以得到高对映选择性和非对映选择性的所需产物。