The formation of a crystalline oxazolidin-5-one from (L)-alanine and its use as a chiral template in the practical synthesis of α-substituted alanine esters
Three different protocols to synthesize oxazolidin-5-ones have been studied with the goal to develop a method to synthesize a diastereomerically pure oxazolidin-5-one. A novel method is reported that uses a dynamic crystallization-induced asymmetric transformation to isolate a single diastereomer of an oxazolidin-5-one in 92% yield on kilogram scale. Alkylation of the oxazolidin-5-one template leads to good-to-excellent yields of N-protected α-substituted alanine esters in >98-99% ee. Schweizerische Chemische Gesellschaft.
Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): Enantiospecific synthesis of α-benzylalanine and hydantoin BIRT-377
N-Isobutoxycarbonyl protected L-alanine was condensed with 4-phenylbenzaldehyde in a crystallization-controlled process to give the corresponding cis-oxazolidinone derivative as the sole product in high yield; this underwent enolization and benzylation wi
Napolitano, Elio,Farina, Vittorio
p. 3231 - 3234
(2007/10/03)
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