In this Research Spotlight episode, Dr. Johannes Lamhauge joins us to share his work on enantioselective synthesis of tropane scaffolds by an organocatalyzed 1,3-dipolar cycloaddition. This episode was editing and hosted by Synthesis Workshop Editorial Board member Andy Tran.
Key reference:
Chem. Eur. J. 2023, 29, e202301830.
doi.org/10.1002/chem.202301830
Additional references (in order of appearance):
For a review on asymmetric tropane synthesis, see: Org. Biomol. Chem. 2021, 19, 3763-3775.
A. R. Katritzky, Y. Takeuchi, J. Am. Chem. Soc. 1970, 92, 4134-4136.
For a review on the cycloadditions of heteroaromatic ring systems, see: A. R. Katritzky, N. Dennis, Chem. Rev. 1989, 89, 827-861.
Examples: Tetrahedron Lett. 2006, 47, 2635-2638; Chem. Lett. 1989, 18, 597-598; Org. Biomol. Chem. 2003, 1, 1884-1893.
Reviews: Angew. Chem. Int. Ed. 2008, 47, 6138-6171; Chem. Soc. Rev. 2009, 38, 2178-2189.
For a review on dienamine catalysis, see: Chem. Soc. Rev. 2016, 45, 6812-6832.
Distortion/interaction-activation model: F. M. Bickelhaupt, K. N. Houk, Angew. Chem., Int. Ed. 2017, 56, 10070-10086.