(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone by lipase-catalyzed resolution of the racemic mixture: New chiral auxiliaries related to pantolactone

Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

“…In sharp contrast, only a few examples of the use of ( R )-pantolactone as chiral auxiliary in 1,3-dipolar cycloadditions have been described, – and the attained levels of asymmetric induction were low to moderate [10−50% diastereomeric excesses (de)]. Several years ago we described the enantioselective synthesis of ( R )- and ( S )-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one [( R )- and ( S )- N -phenylpantolactam, ( R )- and ( S )- 1 , Figure ] as novel chiral auxiliaries, , related to pantolactone, and their efficient use in asymmetric Diels−Alder reactions . However, ( R )- and ( S )- 1 have never been used in 1,3-dipolar cycloadditions.…”

Hydrolases in the Stereoselective Synthesis of N-Heterocyclic Amines and Amino Acid Derivatives

“…Furthermore, the expensive L-pantonolactone is required for the production of the more active ( S )-arylpropionic acids. To avoid these drawbacks, the group of Camps developed the synthesis of new pantolactone related chiral auxiliaries where the key step is a PSL-catalyzed kinetic resolution of the racemic alcohol 59 (Scheme ) . After optimization of the reaction conditions, the biotransformation was performed in a 44 mmol scale (9 g), isolating ( R )- 59 in enantiopure form and high yield.…”