title: Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.
abstract: 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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Stephen N
authors.initials: SN
authors.lastname: Greszler
authors.forename: Justin T
authors.initials: JT
authors.lastname: Malinowski
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000215:Acylation; D006038:Glyoxylates / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D011753:Pyrones; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006038:Glyoxylates; D007783:Lactones; D009943:Organophosphorus Compounds; D011753:Pyrones; D012821:Silanes; C084414:leustroducsin B