Asymmetric Synthesis of Spirocyclic β‐Lactams through Copper‐Catalyzed Kinugasa/Michael Domino Reactions. Issue 34 (18th July 2018)

• Record Type: Journal Article
• Authors: Shu, Tao; Zhao, Long; Li, Sun; Chen, Xiang‐Yu; von Essen, Carolina; Rissanen, Kari; Enders, Dieter
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 34(2018)
• Page Start: 10985
• Page End: 10988
• Publication Date: 2018-07-18
• Subjects: asymmetric synthesis -- copper -- cyclohexadienone -- desymmetrization -- β-lactams; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201806931
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The first copper‐catalyzed highly chemo‐, regio‐, diastereo‐, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne‐tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β‐lactams possessing four contiguous stereocenters, including one quaternary and one tetra‐substituted stereocenter. Abstract : Spiro staircase : Copper‐catalyzed asymmetric Kinugasa/Michael domino reactions of alkyne‐tethered cyclohexadienones and nitrones provide a direct stereoselective approach to spirocyclic β‐lactams possessing four contiguous stereocenters.