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

Timothée Naret | Zendy; Philippe Lesot | Zendy; Andrew R. Puente | Zendy; Prasad L. Polavarapu | Zendy; DavidAlexandre Buisson | Zendy; Jeanne Crassous | Zendy; Grégory Pieters | Zendy; Sophie Feuillastre | Zendy

Open Access

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

Author(s) -

Timothée Naret,

Philippe Lesot,

Andrew R. Puente,

Prasad L. Polavarapu,

DavidAlexandre Buisson,

Jeanne Crassous,

Grégory Pieters,

Sophie Feuillastre

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03219

Subject(s) - chemistry , enantiomer , circular dichroism , optically active , deuterium , molecule , vibrational circular dichroism , quantum chemical , anisotropy , combinatorial chemistry , stereochemistry , computational chemistry , organic chemistry , atomic physics , optics , physics

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 )-[ 2 H]-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 2 H NMR in chiral anisotropic media, their identification was performed by combining quantum chemical calculations and vibrational circular dichroism analysis.

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