Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels-Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons

• Published in: Angewandte Chemie International Edition Vol. 51; no. 9; pp. 2084 - 2087
• Main Authors: Jiang, Xianxing, Shi, Xiaomei, Wang, Shoulei, Sun, Tao, Cao, Yiming, Wang, Rui
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 27.02.2012; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric synthesis; Aza Compounds - chemical synthesis; Catalysis; Chemistry; Chemistry Techniques, Synthetic; Chemistry, Multidisciplinary; Cyclization; cycloadditions; heterocycles; organocatalysis; Physical Sciences; Science & Technology; Spiro Compounds - chemical synthesis; synthetic methods; organocatalysis; CATALYSIS; KETONES; THIOUREAS; asymmetric synthesis; ACID; ENANTIOSELECTIVE SYNTHESIS; heterocycles; cycloadditions; NITRO-MICHAEL ADDITION; AMINE; synthetic methods

Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeleto...