Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 4693-4696 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 57 |
| Issue number | 42 |
| DOIs | |
| Publication status | Published - Oct 19 2016 |
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Keywords
- 6′,6″-Didebromo-cis-3,4-dihydrohamacanthin B
- Aza-Michael addition
- Piperazinone
- α-Amino ester
- β-Substituted nitroalkene
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
A short access to 3,5-disubstituted piperazinones based on the aza-Michael addition of α-amino esters to β-substituted nitroalkenes. / Kudoh, Takayuki; Isoyama, Seiji; Kagimoto, Sachiko; Kurihara, Katsutoshi; Sakakura, Akira.
In: Tetrahedron Letters, Vol. 57, No. 42, 19.10.2016, p. 4693-4696.Research output: Contribution to journal › Article
}
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
PY - 2016/10/19
Y1 - 2016/10/19
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
UR - http://www.scopus.com/inward/record.url?scp=84988649103&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84988649103&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2016.09.015
DO - 10.1016/j.tetlet.2016.09.015
M3 - Article
VL - 57
SP - 4693
EP - 4696
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 42
ER -