Asymmetric Aza-[3 + 3] Annulation in the Synthesis of Indolizidines: An Unexpected Reversal of Regiochemistry

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 annulat...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (16), p.4402-4405
Main Authors: Buchanan, Grant S, Dai, Huifang, Hsung, Richard P, Gerasyuto, Aleksey I, Scheinebeck, Casi M
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Indolizidines - chemical synthesis
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2017438