TY - JOUR
T1 - Stereoselective synthesis of β-amino acid derivatives by asymmetric mannich reaction in flow
AU - Yoshida, Masahito
AU - Umeda, Koji
AU - Doi, Takayuki
N1 - Funding Information:
This work was supported by JSPS KAKENHI ‘Middle-Molecular Strategy’ (JP15H05837) and was partially supported by the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED).
Publisher Copyright:
© 2017 The Chemical Society of Japan.
PY - 2017
Y1 - 2017
N2 - A continuous flow synthesis of β-amino acid derivatives has been demonstrated using an asymmetric Mannich reaction. An enolate of tert-butyl acetate was successfully prepared in 10s at room temperature in a flow reactor, and the desired β-amino acid derivatives were stereoselectively obtained within a short residence time (40 s) in moderate-to-good yields. Sequential Nalkylation of the Mannich product in the flow reactor was also achieved in the presence of DMPU that provided N-alkylated β-amino acid derivatives in good yields.
AB - A continuous flow synthesis of β-amino acid derivatives has been demonstrated using an asymmetric Mannich reaction. An enolate of tert-butyl acetate was successfully prepared in 10s at room temperature in a flow reactor, and the desired β-amino acid derivatives were stereoselectively obtained within a short residence time (40 s) in moderate-to-good yields. Sequential Nalkylation of the Mannich product in the flow reactor was also achieved in the presence of DMPU that provided N-alkylated β-amino acid derivatives in good yields.
UR - http://www.scopus.com/inward/record.url?scp=85031772553&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85031772553&partnerID=8YFLogxK
U2 - 10.1246/bcsj.20170194
DO - 10.1246/bcsj.20170194
M3 - Article
AN - SCOPUS:85031772553
SN - 0009-2673
VL - 90
SP - 1157
EP - 1163
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 10
ER -