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 | Zendy

Magnus Eriksson | Zendy; Elio Napolitano | Zendy; Jinghua Xu | Zendy; Suresh Kapadia | Zendy; Denis Byrne | Zendy; Laurence J. Nummy | Zendy; Nelu Grinberg | Zendy; Sherri Shen | Zendy; HeeWon Lee | Zendy; Vittorio Farina | Zendy

Open Access

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

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 international journal for chemistry

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.

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