Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 29, Pages 4871-4881Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40891d
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Funding
- National Natural Science Foundation of China [21172081]
- Guangzhou Pearl River New Star Plan of Science and Technology Program [2012J2200015]
- Produce and Learning and Research Project of Education Department of Guangdong Province [2011A090200039]
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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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