Peter D. Tiffin

Preparation of enantiomerically enriched aromatic β-amino acids via enzymatic resolution

Abstract A range of enantiomerically enriched aromatic β-amino acids with high e.e. have been prepared via enzymatic resolution of ethyl ester derivatives.

Dispiroketals in synthesis (part 2): A new group for the selective protection of diequatorial vicinal diols in carbohydrates.

Dispiroketal formation as a new method for the selective protection of trans diequatorial vicinal diols in carbohydrate systems is reported.

Oxidation of Activated Halides to Aldehydes and Ketones by N-Methylmorpholine-N-oxide

Abstract N-methylmorpholine-N-oxide (NMO) in acetonitrile solution will oxidise activated primary halides to aldehydes and secondary halides to ketones in good yields at room temperature.

PREPARATION OF (S)-2-QUINOLYLALANINE BY ASYMMETRIC HYDROGENATION

Abstract The synthesis of ( S )-2-quinolylalanine through asymmetric hydrogenation with ( S,S )-Et-DuPHOS-Rh is described. The reaction has been extended to other 2-pyridylalanie derivatives.

A concise, scaleable synthesis of narwedine

Abstract A concise, scaleable synthesis of narwedine from 3,4-dimethoxybenzaldehyde is described. The procedure features a simple modification to the Barton phenolic coupling route.

A novel synthesis of tert-leucine via a Leuckart type reaction

An efficient synthesis of racemic tert-leucine from trimethylpyruvic acid using a Leuckart type reaction is described. A facile resolution of an intermediate with α-methylbenzylamine allows entry into either (R)-or (S)-tert-leucine.

A short, scaleable synthesis of both enantiomers of 2-benzoylsulfanyl-5-phthalimidopentanoic acid from ornithine

Abstract An efficient “one-pot” synthesis of (R)- and (S)-2-bromo-5-phthalimidopentanoic acid from ornithine is described. Subsequent reaction with potassium thiobenzoate affords a concise, scaleable route to (R)- and (S)-enantiomers of 2-benzoylsulfanyl-5-phthalimidopentanoic acid, an intermediate in the synthesis of MMP inhibitors.