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Helicity induction in a bichromophore: a sensitive and practical chiroptical method for absolute configuration determination of aliphatic alcohols

Org Lett. 2002 Nov 28;4(24):4185-8. doi: 10.1021/ol0268079.

Abstract

[reaction: see text] A practical method for the determination of the absolute configuration of aliphatic secondary alcohols, based on the circular dichroism of the readily available N-(1,8-naphthaloyl)-2-aminobenzoyl (NAB) derivative, is presented. The origin of the induced Cotton effects is traced by ab initio calculations to the dominant helicity of the NAB pi-electron system.