title: Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.
abstract: This Perspective describes the discovery and development of silyl glyoxylates, a new family of conjunctive reagents for use in multicomponent coupling reactions. The selection of the nucleophilic and electrophilic components determines whether the silyl glyoxylate reagent will function as a synthetic equivalent to the dipolar glycolic acid synthon, the glyoxylate anion synthon, or the α-keto ester homoenolate synthon. The ability to select for any of these reaction modes has translated to excellent structural diversity in the derived three- and four-component coupling adducts. Preliminary findings on the development of catalytic reactions using these reagents are detailed, as are the design and discovery of new reactions directed toward particular functional group arrays embedded within bioactive natural products.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Gregory R
authors.initials: GR
authors.lastname: Boyce
authors.forename: Stephen N
authors.initials: SN
authors.lastname: Greszler
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
authors.forename: Xin
authors.initials: X
authors.lastname: Linghu
authors.forename: Justin T
authors.initials: JT
authors.lastname: Malinowski
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Satterfield
authors.forename: Daniel C
authors.initials: DC
authors.lastname: Schmitt
authors.forename: Kimberly M
authors.initials: KM
authors.lastname: Steward
mesh_terms: D002384:Catalysis; D006038:Glyoxylates / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006038:Glyoxylates; D007202:Indicators and Reagents; D017646:Organosilicon Compounds