Palladium‐Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit. Issue 25 (2nd May 2014)

• Record Type: Journal Article
• Authors: Li, Qiankun; Fu, Chunling; Ma, Shengming
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 25(2014)
• Page Start: 6511
• Page End: 6514
• Publication Date: 2014-05-02
• Subjects: allenes -- amination -- asymmetric allenylation -- central chirality -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201402647
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A highly enantioselective Pd‐catalyzed amination of allenyl phosphates generating 2, 3‐allenyl amines with central chirality has been developed. Under the optimized conditions, chiral 2, 3‐allenyl amines with or without (an) additional CC double or triple bond(s) have been prepared at 0 °C with up to 90 % yield and 94 % ee by identifying ( R )‐3, 4, 5‐(MeO)3 ‐MeOBIPHEP as the ligand. Abstract : Chiral 2, 3‐allenyl amines with or without (an) additional CC double or triple bond(s) can be prepared through asymmetric Pd‐catalyzed amination of allenyl phosphates. Under the optimized conditions, which involve the use of ( R )‐3, 4, 5‐(MeO)3 ‐MeOBIPHEP as the ligand and the reaction being performed at 0 °C, the products were obtained with up to 90 % yield and 88–94 % ee.