Iridium-catalyzed asymmetric ring-opening of azabicyclic alkenes with alcohols

作者：Yang Dingqiao^*; Xia Jiuyun; Long Yuhua; Zeng Zhongyi; Zuo Xiongjun; Wang Sanyong; Li Chunrong

来源：Organic and Biomolecular Chemistry, 2013, 11(29): 4871-4881.

DOI：10.1039/c3ob40891d

A novel asymmetric ring-opening reaction of N-substituted azabenzonorbornadienes with a wide variety of substituted benzyl alcohols and the addition reaction of N-substituted azabenzonorbornadienes with thiols are reported, affording the corresponding 1,2-trans-alkoxyamino products in moderate yields with excellent enantioselectivities (up to 94% ee) and the corresponding thiol addition products in high yields with lower enantiomeric excesses (ee) in the presence of iridium catalyst, respectively. The effects of ligands, catalyst loading, solvents and additives, and temperature were also investigated. The anti-configuration of the product 3c was confirmed by X-ray crystal structure analysis. A possible mechanism for the present catalytic reaction is proposed.

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  华南师范大学