Facile approach to optically active alpha-alkylidene-beta-amino esters by thermal Overman rearrangement.
A convenient synthetic method for enantioenriched (E)-alpha-alkylidene-beta-amino esters has been developed through thermal Overman rearrangement. Readily accessible (Z)-beta-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 alpha-alkylidene-beta-amino esters via preparation of alpha-alkylidene-beta-lactam derivatives.
Lee
Sung Il
SI
Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
Moon
Soon Young
SY
Hwang
Geum-Sook
GS
Ryu
Do Hyun
DH