Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.
[structure: see text]. We have developed a cationic rhodium(I)/Solphos complex-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition of 1,6-diyne esters with tertiary propargylic alcohols leading to enantioenriched tricyclic 3,3-disubstituted phthalides. The present method represents a versatile new route to the synthesis of enantioenriched tricyclic 3,3-disubstituted phthalides in view of the easy access to both coupling partners.
Tanaka
Ken
K
Department of Applied Chemistry, Graduate School of Engineering, and Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo, Japan. tanaka-k@cc.tuat.ac.jp
Osaka
Takuya
T
Noguchi
Keiichi
K
Hirano
Masao
M
D000480:Alkynes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001572:Benzofurans; D011083:Polycyclic Compounds; D020005:Propanols; C082022:phthalide; D012238:Rhodium; C028255:propargyl alcohol