10.1002/ejoc.201601575
European Journal of Organic Chemistry
COMMUNICATION
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The absolute configuration of product 3a was unambiguously
confirmed by X-ray crystallography and was found to be (2R, 4S)
(Figure 1).[14] The absolute structure of the other dihydropyran
products was thought to be (2R, 4S) by analogy.
2
R
Ph
O
Ph
O
CN
4
S
Ph
3a
Figure 1. X-ray structure of 3a.
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In summary, we have developed a fascinating inverse electron
demand Diels-Alder reaction of linear deconjugated enones
catalyzed by easily available quinine derived primary amine and
benzoic acid.[15] The dihydropyran products having two
stereogenic centres are important frameworks and could be
applied in the synthesis of pharmaceuticals and bioactive natural
products. Investigation of the preparation of other heterocyclic
and carbocyclic rings using this strategy is currently in progress
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Acknowledgements
This work is supported by DST-MPI partner programme. We
thank CIF of Indian Institute of Technology Guwahati for the
instrumental facility.
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Keywords: dihydropyran • organocatalysis • dienamine• inverse
electron-demand Diels-Alder• enantioselectivity
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