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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

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Received: 15 July 2013; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Peng Z, Narcis MJ, Takenaka N. Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts. Molecules. 2013; 18(8):9982-9998.

Chicago/Turabian Style

Peng, Zhili; Narcis, Maurice J.; Takenaka, Norito. 2013. "Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts." Molecules 18, no. 8: 9982-9998.



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