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Fortuitous Enantiomeric SelfâRectification of an Unreported Partial Racemisation in the Synthesis of a Chiral Phosphoric Acid: A Warning to Practitioners.
- 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]
- Subjects :
- *LOW temperatures
*RACEMIZATION
*PHOSPHORYLATION
*BINAPHTHOL
*CHIRALITY
Subjects
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