Chiral gamma, gamma-disubstituted butenolide compound and preparation method thereof

• Main Authors: ZHANG CAIRONG, YAN CHUNA, LIU AIQIN, ZHU WENNING, ZHUGE HUI, BAI ZHUSHUANG, CHEN YONGYI, WANG XINYU, PANG JINGXIANG, LIU XUECHAO
• Format: Patent
• Language: Chinese; English
• Published: 19.06.2020
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention discloses a chiral gamma, gamma-disubstituted butenolide compound and a preparation method thereof. Chiral gamma, gamma-disubstituted butenolide compounds widely exist in various naturalproducts, have important biological activity, and are also important intermediates for constructing polyterpene compounds and medicines. According to the application, a series of chiral gamma, gamma-disubstituted butenolide compounds with the yield as high as 98% and the stereoselectivity greater than 20: 1dr and 99% ee are synthesized through a vinylogous Michael addition reaction of gamma-dimerfuranone catalyzed by a bifunctional thiourea catalyst and alpha, beta-unsaturated nitroolefin. According to the method, the functional gamma, gamma-disubstituted butenolide compound with multiple chiral centers can be conveniently, quickly and efficiently obtained. 本申请公开了一种手性γ，γ-双取代丁烯酸内酯类化合物及其制备方法。手性γ，γ-双取代丁烯酸内酯类化合物广泛存在于各种天然产物中，具有重要生物活性，也是构建多萜类化合物和药物的重要中间体。本申请通过双官能团硫脲类催化剂催化的γ-二聚体呋喃酮与α，β-不饱和硝基烯烃的vinylogous Michael加成反应，合成了