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Reformatsky reagents react sequentially with silyl glyoxylates and β-lactones to give highly functionalized Claisen condensation products. A heretofore undocumented instance of stereochemical 1,4-induction results in efficient transmission of β-lactone stereochemistry to the emerging fully substituted stereocenter. Second-stage transformations reveal that the five heteroatom-containing functionalities embedded within the products are entirely chemo-differentiated, a circumstance that permits rapid assembly of the leustroducsin B core substructure.

journal of the american chemical society

Remote Stereoinduction in the Acylation of Fully Substituted Enolates: Tandem Reformatsky/Quaternary Claisen Condensations of Silyl Glyoxylates and β-Lactones