Divergent synthesis of functionalized carbocycles through organosilane-directed asymmetric alkyne-alkene reductive coupling and annulation sequence.
An organosilane-directed alkyne-alkene reductive coupling of readily available propargylsilanes is used to access densely functionalized chiral allylsilanes. The divergent reactivity of the allylsilanes can be controlled to afford a range of novel carbocyclic ring systems through an intramolecular allylation, [3+2] annulation, and Sakurai-like homodimerization.
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Jie
J
Wu
Yi
Y
Pu
James S
JS
Panek
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D000498:Allyl Compounds; D006844:Hydrocarbons, Cyclic; D012821:Silanes