Min Lu - Organocatalytic Asymmetric alpha-Aminoxylation/Aza-Michael Reactions for the Synthesis of Functionalized Tetrahydro-1,2-oxazines

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  Publication Details (including relevant citation   information):

  Source: Angewandte Chemie-International Edition Volume: 47 Issue:   52 Pages: 10187-10191 Published: 2008

  DOI: 10.1002/anie.200803731


  We have developed a novel, practical, and enantio- and   diastereoselective domino reaction for the

  synthesis of functionalized THOs by using a simple amine   catalyst. The results disclosed herein demonstrate the ability to   control the regio- and stereochemistry of the reaction for the   synthesis of THOs from acyclic substrates. We anticipate that   a-aminoxylation directed domino reactions will have great   potential in the field of organocatalysis. The reaction, which is   easy to perform, proceeds cleanly with complete stereocontrol and   does not require a change in the reaction conditions or adding   reagents. This discovery is likely to be used in synthetic   applications, especially since the a-aminoxylation reaction can   be combined with existing domino methods.

  Address (URL): http://dx.doi.org/10.1002/anie.200803731