Challenging the absence of observable hydrogens in the assignment of absolute configurations by NMR: application to chiral primary alcohols

Abstract

The absolute configuration of β-chiral primary alcohols devoid of observable hydrogens on one of the β-substituents at the asymmetric carbon (L₁/L₂) can be determined by comparison of the ¹H NMR of their (R)- and (S)-9-AMA ester derivatives and analysis of the Δδ^RS for the L substituent and the Cβ-H.