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P‐Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides
Author(s) -
Mohd Aabid,
Anitha Thippani,
Reddy Kallu Rajender,
WencelDelord Joanna,
Colobert Françoise
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901475
Subject(s) - stereocenter , enantiopure drug , kinetic resolution , chemistry , phosphine , enantioselective synthesis , combinatorial chemistry , chiral auxiliary , atropisomer , phosphinate , stereochemistry , organic chemistry , catalysis , fire retardant
Asymmetric synthesis of P ‐stereogenic phosphonates presents a great challenge. Following this target we disclose herein a DKR strategy towards the O–P coupling reaction between an easily accessible enantiopure phenol bearing a chiral sulfinyl auxiliary and a commercially available or easily accessible racemic H‐phosphinate. Although moderate to high chiral induction is achieved, several diastereopure phosphonates can be afforded either by crystallization or flash chromatography. Thus accessed optically pure P ‐stereogenic precursors may be used as appealing building blocks to rapidly assembly original privileged scaffolds as illustrated via the synthesis of a chiral ligand such as PAMPO.