Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines. Issue 3 (3rd December 2015)

• Record Type: Journal Article
• Authors: Martínez, Jose I.; Smith, Joshua J.; Hepburn, Hamish B.; Lam, Hon Wai
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 3(2016)
• Page Start: 1108
• Page End: 1112
• Publication Date: 2015-12-03
• Subjects: allyltrifluoroborates -- asymmetric catalysis -- imines -- isomerization -- rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201508964
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Allylrhodium species derived from δ‐trifluoroboryl β, γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z ‐alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident. Abstract : Migrate to create : Allylrhodium species from δ‐trifluoroboryl β, γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products with two new stereocenters and a Z ‐alkene. A chiral diene ligand leads to products with high enantioselectivities; a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident.