In Situ Enamine Activation in Aqueous Salt Solutions: Highly Efficient Asymmetric Organocatalytic Diels–Alder Reaction of Cyclohexenones with Nitroolefins

In Situ Enamine Activation in Aqueous Salt Solutions: Highly Efficient Asymmetric Organocatalytic Diels–Alder Reaction of Cyclohexenones with Nitroolefins

Deep‐sea Diels–Alder: The asymmetric organocatalytic Diels–Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one‐step concerted addition pathway (see scheme). Deep‐sea Diels–Alder:...

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Veröffentlicht in:Angewandte Chemie International Edition 2009-05, Vol.48 (21), p.3821-3824
Hauptverfasser: Xu, Dan‐Qian, Xia, Ai‐Bao, Luo, Shu‐Ping, Tang, Jie, Zhang, Shuai, Jiang, Jun‐Rong, Xu, Zhen‐Yuan
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
bicyclic systems
Diels–Alder reaction
organocatalysis
water chemistry
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Zusammenfassung:Deep‐sea Diels–Alder: The asymmetric organocatalytic Diels–Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one‐step concerted addition pathway (see scheme). Deep‐sea Diels–Alder: The asymmetric organocatalytic Diels–Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one‐step concerted addition pathway (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900269