title: Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.
abstract: The three-component coupling of Mg acetylides, silyl glyoxylates, and nitroalkenes results in a highly diastereoselective Kuwajima-Reich/vinylogous Michael cascade that provides tetrasubstituted silyloxyallene products. The regio- and diastereoselectivity were studied using DFT calculations. These silyloxyallenes were converted to cyclopentenols and cyclopentitols via a unique Lewis acid assisted Henry cyclization. The alkene functionality present in the cyclopentanol products can be elaborated using diastereoselective ketohydroxylation reactions.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Gregory R
authors.initials: GR
authors.lastname: Boyce
authors.forename: Shubin
authors.initials: S
authors.lastname: Liu
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D006038:Glyoxylates / Q000737:chemistry*; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D006038:Glyoxylates; D009574:Nitro Compounds; C016327:cyclopentanol; D000114:Acetylene