TY - JOUR
T1 - A short access to 3,5-disubstituted piperazinones based on the aza-Michael addition of α-amino esters to β-substituted nitroalkenes
AU - Kudoh, Takayuki
AU - Isoyama, Seiji
AU - Kagimoto, Sachiko
AU - Kurihara, Katsutoshi
AU - Sakakura, Akira
N1 - Funding Information:
This project was financially supported in part by JSPS KAKENHI ( 26410120 ), the Suzuken Memorial Foundation and the Wesco Scientific Promotion Foundation . The authors gratefully thank Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University for the NMR and HRMS measurements.
Publisher Copyright:
© 2016 Elsevier Ltd
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2016
Y1 - 2016
N2 - A simple procedure for the synthesis of chiral 3,5-disubstituted piperazinones is described. The aza-Michael addition of α-amino esters to β-substituted nitroalkenes in an organic/aqueous biphasic solvent system followed by reduction of a nitro group with zinc nanopowder in acidic media and intramolecular ester–amide exchange under heating conditions gives piperazinones in good overall yields. This novel three-step process can provide a short access to a variety of chiral 3,5-disubstituted piperazinones simply by changing the combination of starting nitroalkenes and α-amino esters. This process can be applied to the concise synthesis of the piperazinone-containing natural product 6′,6″-didebromo-cis-3,4-dihydrohamacanthin B.
AB - A simple procedure for the synthesis of chiral 3,5-disubstituted piperazinones is described. The aza-Michael addition of α-amino esters to β-substituted nitroalkenes in an organic/aqueous biphasic solvent system followed by reduction of a nitro group with zinc nanopowder in acidic media and intramolecular ester–amide exchange under heating conditions gives piperazinones in good overall yields. This novel three-step process can provide a short access to a variety of chiral 3,5-disubstituted piperazinones simply by changing the combination of starting nitroalkenes and α-amino esters. This process can be applied to the concise synthesis of the piperazinone-containing natural product 6′,6″-didebromo-cis-3,4-dihydrohamacanthin B.
KW - 6′,6″-Didebromo-cis-3,4-dihydrohamacanthin B
KW - Aza-Michael addition
KW - Piperazinone
KW - α-Amino ester
KW - β-Substituted nitroalkene
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U2 - 10.1016/j.tetlet.2016.09.015
DO - 10.1016/j.tetlet.2016.09.015
M3 - Article
AN - SCOPUS:84988649103
VL - 57
SP - 4693
EP - 4696
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 42
ER -