Resolution of planar chiral cationic (eta6-arene)tricarbonylmanganese complexes.
This contribution describes the first resolution of cationic (eta(6)-arene)Mn(CO)(3) complexes through addition of d-(+)-camphor enolate, isomerization of the stereogenic center, and separation and recrystallization of the corresponding eta(5) diastereoisomers followed by rearomatization and elimination of the chiral auxiliary. This general unprecedented chiral nucleophile addition/elimination (eta(6)-eta(5))/(eta(5)-eta(6)) "round trip" sequence uses a cheap, commercially available chiral nucleophile. As it is compatible with the presence of halide and alkoxy groups, a huge number of applications are envisaged. Some of them, such as the synthesis of enantiopure substituted cyclohexenones, are reported in the present work.
Eloi
Antoine
A
UPMC Univ Paris 06, IPCM, CNRS UMR 7201, Equipe Chimie Organique et Organometallique, Case 181, 4 Place Jussieu, F-75005 Paris, France.
Rose-Munch
Françoise
F
Rose
Eric
E
D001555:Benzene Derivatives / Q000737:chemistry / Q000302:isolation & purification*; D002412:Cations / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D008345:Manganese / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
D001555:Benzene Derivatives; D002412:Cations; D009942:Organometallic Compounds; D008345:Manganese