title: Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification.
abstract: A highly efficient synthesis of enantiomerically pure (S) and (R)-isomers of N-(2,3-dihydroxypropyl)arylamides has been developed with good overall yields in a two step process. The key step involves the ring opening of the chiral epoxide with a nitrogen heterocyclic carbene (NHC) and further rearrangement to chiral N-(2,3-dihydroxypropyl)arylamides in high yields and enantioselectivity. During the reaction, no erosion in chiral purity was observed.
authors.affiliation: Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd, Miyapur, Hyderabad, 500 049, India.
authors.forename: Akula
authors.initials: A
authors.lastname: Raghunadh
authors.forename: Satish S
authors.initials: SS
authors.lastname: More
authors.forename: T Krishna
authors.initials: TK
authors.lastname: Chaitanya
authors.forename: Yadla Sateesh
authors.initials: YS
authors.lastname: Kumar
authors.forename: Suresh Babu
authors.initials: SB
authors.lastname: Meruva
authors.forename: L Vaikunta
authors.initials: LV
authors.lastname: Rao
authors.forename: U K Syam
authors.initials: UK
authors.lastname: Kumar
keywords: N-(2,3-dihydroxypropyl)arylamide; nitrogen heterocyclic carbenes (NHC); oxidative esterification of aromatic aldehyde