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Synfacts 2011(5): 0521-0521
DOI: 10.1055/s-0030-1259823
DOI: 10.1055/s-0030-1259823
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Cascade Diels-Alder/Carbocyclization Approach to Hydrindanes
Y. Han, L. Zhu, Y. Gao, C.-S. Lee*
Peking University Shenzhen Graduate School, P. R. of China
Further Information
Publication History
Publication Date:
15 April 2011 (online)
Significance
The 6,5-fused bicyclic carbocycle motif (hydrindane) is embedded in the backbone of numerous natural products. The authors present a highly convergent approach to cis-hydrindanes utilizing a Lewis acid catalyzed intermolecular Diels-Alder, intramolecular carbocyclization cascade. Zinc bromide was found to be the most efficient catalyst, activating the substrate for both steps of the domino sequence, and providing improved diastereoselectivity over similar zinc species.