Synthesis of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7'-dihydroxy BINOL: Preliminary measurements of the circularly polarized luminescence

M Shyam Sundar; Harish R Talele; Hemant M Mande; Ashutosh V Bedekar; Roberto C Tovar; Gilles Muller

doi:10.1016/j.tetlet.2014.01.108

Synthesis of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7'-dihydroxy BINOL: Preliminary measurements of the circularly polarized luminescence

Tetrahedron Lett. 2014 Mar 1;55(10):1760-1764. doi: 10.1016/j.tetlet.2014.01.108.

Authors

M Shyam Sundar¹, Harish R Talele¹, Hemant M Mande¹, Ashutosh V Bedekar¹, Roberto C Tovar², Gilles Muller²

Affiliations

¹ Department of Chemistry, Faculty of Science, M. S. University of Baroda, Vadodara 390 002, India.
² Department of Chemistry, San José State University, San José, California 95192-0101, USA.

Abstract

Racemic sample of 2,2',7,7'-tetrahydroxy-1,1'-binaphthyl was resolved with (S)-proline and the separated enantiomers were independently converted to atropisomeric bis-oxazines by aromatic Mannich reaction. These chirally pure oxazines were then converted to the helicene like cyclic ethers. The Circularly Polarized Luminescence (CPL) profile was consistent with the isolation of the targeted helical-like molecules in optically pure form, prepared from the achiral primary amines. The compounds of interest displayed active and opposite CPL activities for each sets of the helicene like isomers (P)-/(M)-3 and (P)-/(M)-5.

Keywords: CD and CPL study; Resolution; bis-oxazine.

Abstract

Grants and funding