The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes.
Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products.
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada).
Lei
L
Zhang
Christine M
CM
Le
Mark
M
Lautens
D000080:Acetals / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D000080:Acetals; D000475:Alkenes; D004987:Ethers; D005030:Ethylenes; D007659:Ketones; C008223:ketene
asymmetric catalysis; rhodium; silyl ketene acetals; strained molecules