Diastereoselective conjugate addition of (R)-4-phenyl-2-oxazolidinone to dialkyl alkylidenemalonates

Abstract

The addition of the potassium salt of (R)-4-phenyl-2-oxazolidinone to dialkyl alkylidenemalonates under various conditions is reported. Very good diastereoselectivities (> 90% de) were obtained in several cases. Conversion of one of the adducts to the β-amino acid (S)-β-leucine was achieved in two straightforward steps.

An efficient access to functionally substituted 1,3-oxazolidin-2-ones via cyclization of 1-alkylamino- and 1-arylamino-3-[2-(vinyloxy)ethoxy)]propan-2-ols with dimethyl carbonate

“…11,12 In addition, the oxazolidin-2-one heterocycles are also used as chiral auxiliaries in asymmetric synthesis. 2,3,13,14 Oxazolidin-2-one-containing polymers possess high heat resistance and thermal stability, high elasticity and improved physico-mechanical properties that allow them to be successfully applied as coatings, lacquers, electrically insulating materials, adhesives, foam plastics and so on. 1,[15][16][17][18] Therefore the development of new methods for the synthesis of oxazolidin-2-one derivatives have drawn much attention in recent years.…”