Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made α-Amino Acids.
Described here is an advanced, general method for purely chemical dynamic thermodynamic resolution and S/R interconversion of unprotected tailor-made α-amino acids (α-AAs) through intermediate formation of the corresponding nickel(II)-chelated Schiff bases. The method features virtually complete stereochemical outcome, broad substrate generality (35 examples), and operationally convenient conditions allowing for large-scale preparation of the target α-AAs in enantiomerically pure form. Furthermore, the new type of nonracemizable axially chiral ligands can be quantitatively recycled and reused, rendering the whole process economically and synthetically attractive.
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Shuni
S
Wang
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Shengbin
S
Zhou
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Jiang
J
Wang
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Yong
Y
Nian
Hamari Chemicals Ltd. , 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan.
Aki
A
Kawashima
Hamari Chemicals Ltd. , 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan.
Hiroki
H
Moriwaki
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU , Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain.
José L
JL
Aceña
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU , Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain.|IKERBASQUE, Basque Foundation for Science , Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain.
Vadim A
VA
Soloshonok
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
Hong
H
Liu
D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
D000596:Amino Acids