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Asymmetric Aza-[3+3] Annulation In The Synthesis Of Indolizidines: An Unexpected Reversal Of Regiochemistry.

Grant S. Buchanan, Huifang Dai, R. Hsung, A. Gerasyuto, Casi M. Scheinebeck
Published 2011 · Chemistry, Medicine

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An enantioselective and diastereoselective aza-[3+3] annulation of pyrrolidine-based exo-cyclic vinylogous amides and urethanes with chiral vinyl iminium salts is described. This asymmetric annulation manifold is possible because of an unexpected regiochemical reversal whereby head-to-tail annulations dominated over the predicted head-to-head. It should find prevalent synthetic applications in the enantioselective synthesis of indolizidines.
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