Asymmetric conjugate addition of 5-benzylfurfurals to nitroalkenes using a diaminomethylenemalononitrile organocatalyst

[Display omitted] •Second example for asymmetric direct bisvinylogous conjugate addition with furfural.•All enantioselectivities were higher values in comparison with the previous report.•DMM skeleton developed by us is excellent motif for organocatalysis. A pyrrolidine–diaminomethylenemalononitrile...

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Bibliographic Details
Published in:Tetrahedron letters 2017-12, Vol.58 (51), p.4759-4762
Main Authors: Akutsu, Hiroshi, Nakashima, Kosuke, Hirashima, Shin-ichi, Kitahara, Moeko, Koseki, Yuji, Miura, Tsuyoshi
Format: Article
Language:English
Subjects:
5-Benzylfurfural
Conjugate addition
Diaminomethylenemalononitrile
Nitroalkene
Organocatalyst
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Summary:[Display omitted] •Second example for asymmetric direct bisvinylogous conjugate addition with furfural.•All enantioselectivities were higher values in comparison with the previous report.•DMM skeleton developed by us is excellent motif for organocatalysis. A pyrrolidine–diaminomethylenemalononitrile organocatalyst efficiently promotes the asymmetric direct bisvinylogous Michael addition of 5-benzylfurfural derivatives to nitroalkenes, affording the corresponding ε-regioselective addition products in high yields with up to 86% ee.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.10.078