4.8 Article

Iridium-Catalyzed Asymmetric Ring-Opening Reactions of N-Boc-azabenzonorbornadiene with Secondary Amine Nucleophiles

Journal

ORGANIC LETTERS
Volume 10, Issue 21, Pages 4723-4726

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801768e

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Funding

  1. National Natural Science Foundation of China [20772036]
  2. Natural Science Foundation Guangdong Province [8251063101000002, 7005804]

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Iridium-catalyzed asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with a number of secondary amines has been developed for the first time. The reaction gave 1,2-trans-diamine derivatives in moderate to good yields with high enantioselectivity in the presence of 2.5 mol % of [lr(COD)Cl](2) and 5 mol % of (S)-BINAP. The trans-configuration of the 1,2-diamino products was confirmed by X-ray crystallography.

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