Silyl-substituted spirodiepoxides: stereoselective formation and regioselective opening.
A short synthesis of the natural product epi-citreodiol and the method developed to gain access to this target are described. Key advances focus on silyl substituted allenes. Upon exposure to dimethyldioxirane, spirodiepoxides form with high face selectivity and subsequently react at the silyl terminus.
Ghosh
Partha
P
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA.
Cusick
Joseph R
JR
Inghrim
Jennifer
J
Williams
Lawrence J
LJ
D004852:Epoxy Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004852:Epoxy Compounds; D013141:Spiro Compounds