Fortuitous enantiomeric self‐rectification of an unreported partial racemisation in the synthesis of a chiral phosphoric acid: a warning to practitioners
Author(s)
Lancaster, Ben Michael John
White, Andrew JP
Braddock, D Christopher
Type
Journal Article
Abstract
Racemisation without Consequence: MOM deprotection of an ether intermediate during a routine synthesis of phosphoric acid 1 promoted partial racemisation of the product BINOL 5. Surprisingly, however, after phosphorylation of the partially racemised BINOL, enantiopure acid 1 was isolated. Further inspection revealed that during phosphorylation, unhydrolysed racemic phosphorochloridate 6 precipitated, thus restoring homochirality in the product phosphoric acid 1. 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.
Date Issued
2024-12
Date Acceptance
2024-10-01
Citation
Chemistry – A European Journal, 2024, 30 (72)
ISSN
0947-6539
Publisher
Wiley
Journal / Book Title
Chemistry – A European Journal
Volume
30
Issue
72
Copyright Statement
© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Identifier
http://dx.doi.org/10.1002/chem.202403318
Publication Status
Published
Article Number
e202403318
Date Publish Online
2024-10-10