Open AccessThe 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
Author(s) -
Magnus Eriksson,
Elio Napolitano,
Jinghua Xu,
Suresh Kapadia,
Denis Byrne,
Laurence J. Nummy,
Nelu Grinberg,
Sherri Shen,
Heewon Lee,
Vittorio Farina
Publication year - 2006
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2006.566
Subject(s) - diastereomer , alanine , yield (engineering) , crystallization , alkylation , chemistry , transformation (genetics) , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , amino acid , materials science , biochemistry , metallurgy , gene
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 ?-substituted alanine esters in >98–99% ee.