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Updated: Mar 13, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Exocyclic C=C Bonds
Jingzhao Xia1, Guoqiang Yang2, Ruijing Zhuge2
1School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.
Abstract:
An iridium-catalyzed asymmetric hydrogenation of unfunctionalized exocyclic C=C bonds was performed by using an axially flexible chiral phosphine-oxazoline ligand, providing the desired chiral 1-benzyl-2,3-dihydro-1H-indene products with up to 98 % ee (enantiomeric excess). This represents the first general hydrogenation of unfunctionalized exocyclic olefins with high selectivity reported thus far. The additive acetate ion plays an important role in the reaction's high enantioselectivity. The chiral product can be further transformed into key intermediates required for the synthesis of an important insecticide and a drug compound.
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