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Fortuitous Enantiomeric Self‐Rectification of an Unreported Partial Racemisation in the Synthesis of a Chiral Phosphoric Acid: A Warning to Practitioners.

Authors :
Lancaster, Ben M. J.
White, Andrew J. P.
Christopher Braddock, D.
Source :
Chemistry - A European Journal. Oct2024, p1. 7p. 9 Illustrations.
Publication Year :
2024

Abstract

<bold>Racemisation without Consequence</bold>: MOM deprotection during a routine synthesis of phosphoric acid <bold>1</bold> promoted partial racemisation of the product BINOL <bold>5</bold>. Surprisingly, however, after phosphorylation of the partially racemised BINOL, <italic>enantiopure</italic> acid <bold>1</bold> was isolated. Further inspection revealed that during phosphorylation, unhydrolysed racemic phosphorochloridate <bold>6</bold> precipitated, thus restoring homochirality in the product phosphoric acid <bold>1</bold>. Moreover, MOM deprotection partial racemisation was avoided by conducting reactions at lower temperatures for no longer than the required deprotection time, and/or by application of other deprotection conditions from the literature. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09476539
Database :
Academic Search Index
Journal :
Chemistry - A European Journal
Publication Type :
Academic Journal
Accession number :
180762219
Full Text :
https://doi.org/10.1002/chem.202403318