Premium
Diastereoselective Hydrolysis of Asymmetric P–Cl Species and Synthesis of Optically Pure ( R P )‐(–)‐Menthyl H‐Phenylphosphinate
Author(s) -
Wang WeiMin,
Liu LiJuan,
Zhao ChangQiu,
Han LiBiao
Publication year - 2015
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.201500126
Subject(s) - chemistry , diastereomer , phosphorus trichloride , hydrolysis , menthol , yield (engineering) , optically active , medicinal chemistry , phosphorus , organic chemistry , stereochemistry , metallurgy , materials science
Phenyl dichlorophosphine reacted with ( L )‐(–)‐menthol to afford two diastereomers of menthyl phenylphosphinate ( R P )‐ 1a /( S P )‐ 1a′ in up to 89:11 dr . Compound ( R P )‐ 1a was isolated in 58 % yield (60 g) and > 99:1 dr . An HCl‐promoted diastereoselective hydrolysis of the P–Cl species was found to be involved in the reaction. On the basis of this, a mixture of 1a / 1a′ with 50:50 dr was converted to a mixture enriched in 1a with 88:12 dr by treatment with phosphorus trichloride.