Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide | Zendy

Silvia Vera | Zendy; Ana María Vázquez | Zendy; Ricardo Rodrı́guez | Zendy; Sandra del Pozo | Zendy; Iñaki Urruzuno | Zendy; Abel de Cózar | Zendy; Antonia Mielgo | Zendy; Claudio Palomo | Zendy

Open Access

Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide

Author(s) -

Silvia Vera,

Ana María Vázquez,

Ricardo Rodrı́guez,

Sandra del Pozo,

Iñaki Urruzuno,

Abel de Cózar,

Antonia Mielgo,

Claudio Palomo

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00406

Subject(s) - glycine , schiff base , aldol reaction , catalysis , chemistry , base (topology) , amino acid , stereochemistry , medicinal chemistry , organic chemistry , mathematics , biochemistry , mathematical analysis

Here we report the highly enantio- and syn -selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Brønsted base (BB) catalysis. The key of this approach is the use of benzophenone-derived imine of glycine o -nitroanilide as a pronucleophile, where the o -nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research