Diastereoselection through chiral conformations.
Chiral conformations of flexible molecules may develop in a concerted manner if the molecule is crowded enough to assure sufficient level of through-the-space contacts. Higher number (> 4) of groups connected to the same atom, as in many coordination compounds, can be advantageous in this respect. The case study of R,S-[(sec-butoxycarbonyl)methyl]cobalt tricarbonyl triphenylphosphine is presented here. X-ray diffraction shows that the possible number of enantiomeric and diastereomeric conformations is reduced by 75% (from 8 to 2) by concerted development of the molecular conformations in crystalline phase.
Szabó
M
M
Müller Laboratory, Department of Organic Chemistry, University of Veszprém, Egyetem-u.6, H-8200 Veszprém, Hungary.
Szilágyi
R
R
Bencze
L
L
Boese
R
R
Zucchi
C
C
Caglioti
L
L
Pályi
G
G
D003035:Cobalt / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D010720:Phosphines; D003035:Cobalt