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

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      Publication Details (including relevant citation   information):

      Angew.   Chem. Int. Ed. 47, 10187   (2008). (highlighted by Organic Chemistry Portal)




                Catalyst             for THOught: The title reaction using acyclic             nitroalkenals for the asymmetric installation of both             C[BOND]O               and C[BOND]N               bonds led to functionalized tetrahydro-1,2-oxazines               (THOs) having up to three stereogenic centers; the               products were isolated in up to 90 % yield with               excellent enantioselectivity and complete               diastereoselectivity (see scheme). DFT calculations               reveal an unprecedented transition state containing a               molecule of water, which assists in the C[BOND]N               bond-forming step by participating in two hydrogen               bonds.            


      Address (URL): http://onlinelibrary.wiley.com/doi/10.1002/anie.200803731/abstract