American Chemical Society
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Facile Approach to Optically Active α-Alkylidene-β-amino Esters by Thermal Overman Rearrangement

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journal contribution
posted on 2010-07-16, 00:00 authored by Sung Il Lee, Soon Young Moon, Geum-Sook Hwang, Do Hyun Ryu
A convenient synthetic method for enantioenriched (E)-α-alkylidene-β-amino esters has been developed through thermal Overman rearrangement. Readily accessible (Z)-β-branched Morita−Baylis−Hillman esters serve as chiral pool precursors. Thermal rearrangement proceeded through a concerted pseudopericyclic transition state to produce (E)-stereoselective products. We expanded the synthetic utilities of α-alkylidene-β-amino esters via preparation of α-alkylidene-β-lactam derivatives.