The synthesis of (S)-5-(tosylmethyl)-2-pyrrolidinone from (S)-pyroglutaminol [(S)-2-(hydroxymethyl)-2-pyrrolidinone] in three steps and its applications into the synthesis of indolizidines is described in this communication.

Polymer-supported cinchona alkaloid salts with different spacers were used as phase transfer catalysts in the asymmetric C-alkylation of N-diphenyl methylene glycine t-butyl ester for the synthesis of phenylalanine. Various catalysts and alkylation conditions were studied, the best result being 81% ee with cinchoninium iodide bound to polystyrene with a four carbon spacer.

The regio- and diastereoselectivities of epoxidations of decalin-1,4 -dienones and dienols obtained from the Birch reduction alkylation of different a-tetralones is described. They appear to depend on the steric approach control of the peracid and show an important contribution of the directing effect of homoallylic alcohols

Addition of selected organo-zinc halides to N-phenyl Benzenesulfonimine with a copper catalyst under mild conditions leads to substituted sulfonamides. Although experimental conditions and workup have not been optimized, best yields have been obtained when using benzyliczinc halides.

A highly stereoselective enantiodivergent synthesis of non-racemic 3,3,3-trifluoroalanine 7 is reported. The methodology is based on the reduction of the sulfinimine 3 derived from ethyl trifluoropyruvate, followed by acidic hydrolysis of the resulting diastereomeric sulfinamides 4 and 5.

The combination of biocatalysis and transition metal catalysis provides a powerful and versatile pathway for the synthesis of multifunctional building blocks. In this approach, the biocatalyst is used to generate enantiomerically pure starting materials, while transition metals are used in a catalytic fashion for further synthetic elaboration.

A correlation between the solvent polarity and the logarithm of the diastereoisomer ratio (dr) was found for the uncatalyzed [4+2] cycloaddition of cyclopentadiene to N,N'-fumaroyldi[(2R)-bornane-10,2-(2'phenyl-pyrazol-3'-one)]. Using the Abboud-Abraham-Kamlet-Taft parameters, predictive values for this method, allowed an optimum diastereoisomeric excess (de) of 94% in CHCl3. Implications for the stereochemical course of the reaction as well as a comparison with the (2R)-bornane-10,2-sultam analogous auxiliary are discussed.

Several non-proteinogenic amino acids containing the pyrrolidine ring show high affinity towards NMDA (N-methyl-D-aspartic acid) and glutamate receptors. Thus, they can be employed in order to establish the mechanisms involved in transmission of nerve impulse. Moreover, they can be used for treatmentment of CNS diseases. Among them, 2- carboxy-3-pyrrolidinacetic acid (CPAA), 1, and the diastereomeric 2-carboxy-4-(2-methoxyphenyl)-3- pyrrolidineacetic acids 2 and 3 are significant examples

The preparation of two new chiral binaphthyl phosphorous ligands bearing perfluorinated ponytails is reported. Special precautions or harsh reaction conditions were not required and the fluorous ligands were readily isolated from by-products.

Cyclization of the title compounds may occur in various ways (e.g., with the participation of C-6 or C-4 atom of the pyridazinone ring) to form differently fused pyridazino ring systems. The regiochemistry was found to be particularly dependent on the length of the side chain: from the hydroxyethylamino derivatives pyridazino[3,4-b]oxazines, and from hydroxypropylamino derivatives pyridazino[3,4-b]oxazepine and pyridazino[4,5-b]oxazepine systems were formed.