Di(1-naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

Jun Zhang; Wei Sheng; Hadi Gholami; Tatsuo Nehira; Babak Borhan

doi:10.1002/chir.22775

Di(1-naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

Chirality. 2018 Feb;30(2):141-146. doi: 10.1002/chir.22775. Epub 2017 Nov 8.

Authors

Jun Zhang¹, Wei Sheng¹, Hadi Gholami¹, Tatsuo Nehira², Babak Borhan¹

Affiliations

¹ Department of Chemistry, Michigan State University, East Lansing, Michigan, USA.
² Graduate School of Integrated Arts and Sciences, Hiroshima University, Hiroshima, Japan.

PMID: 29114933
DOI: 10.1002/chir.22775

Abstract

The absolute stereochemistry of chiral carboxylic acids is determined as a di(1-naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton-coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

Keywords: ECCD; absolute stereochemistry; carboxylic acids; chiral sensing; chirality; computational analysis.