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Molecules 2013, 18(8), 9982-9998; doi:10.3390/molecules18089982
Article

Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts

,  and *
Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146, USA
* Author to whom correspondence should be addressed.
Received: 15 July 2013 / Revised: 13 August 2013 / Accepted: 14 August 2013 / Published: 19 August 2013
(This article belongs to the Special Issue Asymmetric Catalysis)
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Abstract

Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.
Keywords: asymmetric catalysis; nitroalkene; Diels-Alder reaction; helical chirality asymmetric catalysis; nitroalkene; Diels-Alder reaction; helical chirality
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Peng, Z.; Narcis, M.J.; Takenaka, N. Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts. Molecules 2013, 18, 9982-9998.

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