Desymmetrization of meso-cyclic imides via enantioselective monohydrogenation.
meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88-97% ee using trans-[Ru((R)-BINAP)(H)(2)((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.
Takebayashi
Satoshi
S
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
John
Jeremy M
JM
Bergens
Steven H
SH
D002384:Catalysis; D006865:Hydrogenation; D007094:Imides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007094:Imides