Enantioselective Organocatalytic One‐Pot Amination/aza‐Michael/Aldol Condensation Reaction Sequence: Synthesis of 3‐Pyrrolines with a Quaternary Stereocenter |
| |
Authors: | Alaric Desmarchelier Dr Vincent Coeffard Dr Xavier Moreau Prof Christine Greck |
| |
Institution: | Institut Lavoisier de Versailles,UMR CNRS 8180, Université de Versailles Saint‐Quentin‐en‐Yvelines, 45, Avenue des Etats‐unis, 78035 Versailles Cedex (France), Fax: (+33)?1‐39‐25‐44‐52 |
| |
Abstract: | Primary amine‐catalyzed direct conversion of α,α‐disubstituted aldehydes into 3‐pyrrolines with a quaternary stereocenter is reported. The one‐pot enantioselective sequence is based on a α‐amination, an aza‐Michael addition of hydrazine, an aldol condensation dehydratation and proceeds with good yields and excellent levels of enantioselectivity. Synthetically attractive applications including the formation of aziridinopyrrolidine or epoxypyrrolidine derivatives with good yields and selectivities are also described. |
| |
Keywords: | hydrazine one‐pot reaction organocatalysis pyrrolines synthetic methods |
|
|