Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: highly efficient synthesis of enantiopure (-)-erythrodiene.
Easily prepared allyl phenyl sulfones, capable of introduction of the alkene by electrophilic alpha-substitution, are superior to allyl acetates as substrates for Pd-catalyzed Zn-ene cyclizations, providing C5 or C(4)N rings with cis-1,2-vinyl and -CH(2)Zn substituents. Several examples, with different methods of substrate preparation, are presented. [reaction: see text]
Deng
Kai
K
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Chalker
Justin
J
Yang
Ao
A
Cohen
Theodore
T
D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
D000498:Allyl Compounds; D013141:Spiro Compounds; D013450:Sulfones; C511223:erythrodiene; D010165:Palladium; D015032:Zinc