ChemInform Abstract: Diastereoselective Ortholithiation and Conformational Control in Stereospecific Dearomatizing Anionic Cyclizations.
Abstract
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ChemInform Abstract
The mechanism of the stereoselectivity of the dearomatizing anionic cyclization of naphthamides like (I) is studied. It is shown by several control experiments, that the starting naphthamides exist as a mixture of two atropisomers at -78 °C, from which only one isomer is able to undergo lithiation and cyclization reaction. Quenching with an electrophile then furnishes naphtho-fused pyrrolidinones like (II) with absolute stereoselectivity.
