Open AccessSynthesis 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 -
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) - chemistry , imine , benzophenone , glycine , schiff base , aldol reaction , nucleophile , catalysis , reactivity (psychology) , aldimine , amino acid , brønsted–lowry acid–base theory , stereochemistry , organic chemistry , combinatorial chemistry , medicinal chemistry , medicine , biochemistry , alternative medicine , pathology
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.