OPTICAL RESOLUTION AND ABSOLUTE-CONFIGURATION OF THE CHIRAL PENTAMETHYLCYCLOPENTADIENYLRHENIUM CARBONYL COMPLEX [(ETA-5-C5ME5)RE(NO)(PPH3)(CO)]+BF4- Academic Article uri icon

abstract

  • Reaction of racemic ester (5-C5Me5)Re(NO)(PPh3)(CO2CH3) and (-)-(S)--(1-naphthyl)ethylamine gives amide (5-C5Me5)Re(NO)(PPh3)(CONHCH(CH3) C10H7) (3) as a (SS)-/(RS)- diastereomer mixture. Crystallization gives the less soluble diastereomer (-)-(RS)-3 (77%, 98% diastereomeric excess). Subsequent reaction with CF3CO2H and then NaBF4 gives carbonyl complex (-)-(R)-[(5-C5Me5)Re(NO)(PPh3)(CO)]+ BF4- (91%, 99% enantiomeric excess), which is in turn reduced (Li(C2H5)3BH/BH3 THF) to methyl complex (-)-(R)-(5-C5Me5)Re(NO)(PPh3)(CH3) (97%). These serve as convenient precursors to a variety of other optically active complexes. Preparations of enantiomeric complexes, diastereomer (-)-(RR)-3, and recycling of the chiral -(1-naphthyl)ethylamine auxilliary are also described. The structure and absolute configuration of (-)-(RS)-3 is verified crystallographically (orthorhombic, P212121 (no. 19), a 12.348(4), b 13.198(5), c 22.168(9) , Z = 4). 1990.

published proceedings

  • JOURNAL OF ORGANOMETALLIC CHEMISTRY

author list (cited authors)

  • HUANG, Y. H., NIEDERCORN, F., ARIF, A. M., & GLADYSZ, J. A.

citation count

  • 12

complete list of authors

  • HUANG, YH||NIEDERCORN, F||ARIF, AM||GLADYSZ, JA

publication date

  • February 1990