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Synlett 2016; 27(04): 551-554
DOI: 10.1055/s-0035-1560547
DOI: 10.1055/s-0035-1560547
cluster
31P NMR Based Method for Determining Enantiopurity of Chiral Phosphoric Acids and Its Application to the BINOL- and H8-BINOL-Based Chiral Phosphoric Acid Thermal Racemization Studies
Further Information
Publication History
Received: 01 September 2015
Accepted after revision: 02 November 2015
Publication Date:
30 November 2015 (online)


We dedicate this Letter to Professor James D. White on the occasion of his 80th birthday
Abstract
A simple and reliable protocol for determining the enantiopurity of 3,3′-substituted BINOL- and H8-BINOL-based chiral phosphoric acids (CPA) using 31P NMR spectroscopy in the presence of chiral amines as the discriminating agents is described. The generality of this method is demonstrated using nine common BINOL- and H8-BINOL-based chiral acids. This technique was utilized for monitoring the extent of racemization of 3,5-(F3C)2C6H3-substituted BINOL- and H8-BINOL-based CPA at 200, 220, and 250 °C.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560547.
- Supporting Information