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Synfacts 2011(2): 0189-0189  
DOI: 10.1055/s-0030-1259269
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Catalyzed Enantioselective Ring Opening of Azanorbornene Derivatives

Contributor(s): Hisashi Yamamoto, Zhi Li
Y. Long, D. Yang*, Z. Zhang, Y. Wu, H. Zeng, Y. Chen*
South China Normal University, Guangzhou, P. R. of China and City University of New York, USA
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

In this report the authors described an iridium-catalyzed asymmetric ring opening of 7-azabenzonorbornene derivatives to generate trans-1,2-diamines. The reaction undergoes an ­iridium-catalyzed nucleophilic substitution of one of the two allylic positions in the azanorbornene structure. The symmetric substrate is thus desymmetrized to generate chiral products in good enantioselectivities.