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Synfacts 2010(4): 0446-0446  
DOI: 10.1055/s-0029-1219475
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Benzoazepines through Allylic Substitution

Contributor(s): Mark Lautens, Jane Panteleev
H. He, W.-B. Liu, L.-X. Dai, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsdatum:
22. März 2010 (online)

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Significance

The authors describe an efficient synthesis of chiral benzoazepines through a double allylic substitution reaction. This work further demonstrates the wide applicability and utility of asymmetric iridium-catalyzed allylic substitutions as pioneered by Helmchen and Hartwig (see Review below). Compounds featuring this structural motif possess diverse biological activity and asymmetric methods towards their synthesis are noteworthy.

Review: For a review on allylic substitutions, see: R. Takeuchi, S. Kezuka Synthesis 2006, 3349-3366.