Gamma-allyl phosphinoyl phenyl sulfone (GAPPS): a conjunctive reagent for the synthesis of EE, EZ, and ET 1,3-dienes.
A three-operation conjunctive strategy is available for the synthesis of EE, EZ, and ET dienes. This protocol employs a sequential Wadsworth-Emmons reaction using a GAPPS reagent followed by alkylation of an allylic sulfone anion, and finally ligand-mediated, palladium-catalyzed desulfonylation.
Li
Xiaojin
X
Department of Chemistry, 560 Oval Drive, Purdue University, West Lafayette, IN 47907, USA.
Lantrip
Douglas
D
Fuchs
Philip L
PL
D000475:Alkenes / Q000138:chemical synthesis*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D000475:Alkenes; D000498:Allyl Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005231:Fatty Acids, Unsaturated; C481034:Gamma-allyl phosphinoyl phenyl sulfone; D018942:Macrolides; D013450:Sulfones; C421091:callystatin A; C449042:scytophycin C; C114125:apoptolidin