Chemical Synthesis of [ 2 H]-Ethyl Tosylate and Exploration of Its Crypto-optically Active Character Combining Complementary Spectroscopic Tools

Timothée Naret (1) , Philippe Lesot (2) , Andrew Puente (3) , Prasad Polavarapu (3) , David-Alexandre Buisson (1) , Jeanne Crassous (4) , Grégory Pieters (1) , Sophie Feuillastre (1, 5, 6)

1 SCBM - Service de Chimie Bio-Organique et de Marquage
2 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
3 Vanderbilt University [Nashville]
4 ISCR - Institut des Sciences Chimiques de Rennes
5 MTS - Médicaments et Technologies pour la Santé
6 LMT2 - LMT équipe 2

Small chiral molecules are excellent candidates to push the boundaries of enantiodiscrimination analytical techniques. Here is reported the synthesis of two new deuterated chiral probes, (R)- and (S)-[2H]-ethyl tosylate, obtained with high enantiomeric excesses. Due to their crypto-optically active properties, the discrimination of each enantiomer is challenging. Whereas their enantiopurity is determined by 2H NMR in chiral anisotropic media, their identification was performed by combining quantum chemical calculations and vibrational circular dichroism analysis.

Mots clés: Absolute configuration; 2H-NMR; VCD analysis; Chiral oriented media; QC calculations; Enantiopurity; Crypto-chirality

Domaines: Chimie organique; Chimie analytique

Timothée Naret, Philippe Lesot, Andrew Puente, Prasad Polavarapu, David-Alexandre Buisson, et al.. Chemical Synthesis of [ 2 H]-Ethyl Tosylate and Exploration of Its Crypto-optically Active Character Combining Complementary Spectroscopic Tools. Organic Letters, 2020, 22 (22), pp.8846-8849. ⟨10.1021/acs.orglett.0c03219⟩. ⟨hal-02987518v2⟩