Highly diastereoselective synthetic route to enantiopure beta(2)-amino acids and gamma-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary.

The alkylation reactions of an amide enolate derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur with a complete diastereoselectivity and in good yields with various electrophiles. This reaction provides a versatile and straightforward strategy for the synthesis of beta(2)-amino acids and gamma-amino alcohols in enantiopure form.

A convenient synthesis of gamma-functionalized cyclopentenones.

The synthesis of gamma-functionalized cyclopentenones was carried out in a few steps, starting firstly with the preparation of nitroketonic intermediates 2, which were readily transformed into 1,4-diketones using the Nef conversion. The intramolecular cyclization of the gamma-diketones 3 in a basic medium, led to the functionalized cyclopentenones 4.