Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride. Issue 10 (27th January 2017)

• Record Type: Journal Article
• Authors: Jarvis, Claire L.; Hirschi, Jennifer S.; Vetticatt, Mathew J.; Seidel, Daniel
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 10(2017)
• Page Start: 2670
• Page End: 2674
• Publication Date: 2017-01-27
• Subjects: anion binding -- asymmetric catalysis -- hydrogen bonding -- ion pairing -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201612148
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An amide‐thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N ‐aryl and N ‐alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio‐ and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations. Abstract : Get it together : An amide‐thiourea compound, operating through a novel ion‐pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N ‐aryl and N ‐alkyl imines readily undergo the formal [4+2] cycloaddition to provide lactams with high levels of enantio‐ and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.