Optical rotatory dispersion studies. 137. Synthesis and chiroptical properties of α- and β-deuterium substituted aliphatic aldehydes and ketones

The synthesis and chiroptical properties of (2R)-2-deuterio-3-hexanone (8a), (2R)-2-deuterio-4-methylpentanone (8b), (2R)-2-deuteriopentanal (9a), (2R)-2-deuterio-3-methylbutanal (9b), and (3R)-3-deuteriohexanal (13) are described. All exhibit Cotton effects consistent with the preferred eclipsed conformation of the carbonyl/α-alkyl moiety. The β-deuterio aldehyde 13 shows a sign change in accordance with the proximity rule previously observed in CD studies