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Synthesis 2019; 51(04): 865-873
DOI: 10.1055/s-0037-1611295
DOI: 10.1055/s-0037-1611295
paper
Harvesting New Chiral Phosphotriesters by Phosphorylation of BINOL and Parent Bis-phenols
This work was supported by Université de Rennes 1, CNRS, Rennes Métropole, and Région Bretagne.
Further Information
Publication History
Received: 31 August 2018
Accepted after revision: 04 October 2018
Publication Date:
25 October 2018 (online)
Abstract
A systematic study on the phosphorylation of BINOL and other bis-phenols with chlorophosphates is described. An intriguing reactivity has been observed that is attributable to the hydroxyl group acidity and to the leaving group nucleofuge character within the phosphorylating agent used. By playing on these two parameters, new chiral monophosphotriesters, symmetrical homo-BINOL bisphosphates, and unsymmetrical non-homo-BINOL derivatives incorporating a non-chiral side unit, were synthesized selectively and in good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611295.
- Supporting Information
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For the synthesis of BINOL phosphorochloridate 17, see: