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. 2013 Aug 19;18(8):9982-98.
doi: 10.3390/molecules18089982.

Enantio- and periselective nitroalkene Diels-Alder reactions catalyzed by helical-chiral hydrogen bond donor catalysts

Zhili Peng  1 , Maurice J Narcis, Norito Takenaka
Affiliations

Enantio- and periselective nitroalkene Diels-Alder reactions catalyzed by helical-chiral hydrogen bond donor catalysts

Zhili Peng et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
A proven strategy for the synthesis of cyclopentenes.
Figure 1
Figure 1
(M)- and (P) catalysts used.
Scheme 2
Scheme 2
Two endo TS models with (M)-catalyst. Non-substituted CP is shown for clarity.
Scheme 3
Scheme 3
A three-step synthesis of a new class of dienes 1.
See this image and copyright information in PMC

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