一种由 squaramide 催化的不对称级联迈克尔加成/酰基转移反应，涉及不饱和苯并噻吩酮和α-硝基酮。
A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones.
机构信息
Key Laboratory of Medical Molecule Science & Pharmaceutics Engineering, Ministry of Industry and Information Technology, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No. 5 Zhongguancun South Street, Beijing 100081, People's Republic of China.
出版信息
Org Biomol Chem. 2022 Jan 26;20(4):840-846. doi: 10.1039/d1ob02217b.
An efficient and practical organocatalytic asymmetric strategy was developed using unsaturated benzothiophenones and α-nitroketones catalysed by bifunctional squaramide Michael addition and acyl transfer steps. A broad range of chiral acyloxybenzothiophene derivatives were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 98% ee). What's more, employing different chiral squaramide catalysts and unsaturated benzothiophenones can deliver the acyloxy unit at the 2-position or 3-position of benzothiophene.
发展了一种使用不饱和苯并噻吩酮和α-硝基酮的高效实用的有机催化不对称策略，该策略由双功能脒催化迈克尔加成和酰基转移步骤。通过该策略，可以获得广泛的手性苯并噻吩并[2,3-d]恶唑啉衍生物，产率高（高达 97%），对映选择性好（高达 98%ee）。此外，采用不同的手性脒催化剂和不饱和苯并噻吩酮，可以将酰氧基单元引入苯并噻吩的 2-位或 3-位。
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