Diastereoselective and Enantioselective Michael Addition Reactions of Ketones and Aldehydes to Nitro Olefins Catalyzed by C-2-Symmetric Axially-Unfixed Biaryl-Based Organocatalysts Derived from Enantiopure alpha-Proline

作者：Zhao, Hong-Wu^*; Li, Hai-Long; Yue, Yuan-Yuan; Sheng, Zhui-Hui

来源：European Journal of Organic Chemistry, 2013, 2013(9): 1740-1748.

DOI：10.1002/ejoc.201201306

• Synthetic methods
• C-C coupling
• Organocatalysis
• Michael addition
• Nitrogen heterocycles
• Enantioselectivity
• Diastereoselectivity

A new class of axially-unfixed biaryl-based pyrrolidines with C-2-symmetry were designed and synthesized by using enantiopure alpha-proline as a chiral source. These bifunctional organocatalys provided Michael adducts in high chemical yields (up to 99%) and with excellent stereoselectivities (up to 99: 1 dr and 96% ee) in the direct Michael addition reactions of a variety of ketones and aldehydes to nitro olefins. The transition states were proposed to clarify the stereochemical course of the examined reactions.

• 出版日期2013-3
• 单位北京工业大学