Abstract
Condensation of 2-acetyl benzoic acid with l-cysteine esters proceeds with extremely high diastereoselectivity to produce the desired thiazolo[2,3- a]isoindolin-1-one products in good yield. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystallography. Stereoselective enolate alkylation of this substrate has been investigated as a method to manipulate the ring skeleton, and was found to proceed with up to exclusive levels of stereoselectivity.
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