Abstract
β,β-Disubstituted β-amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration. Based on this methodology, a total synthesis of manzacidins A and C has been achieved.
| Original language | English |
|---|---|
| Journal | Asian Journal of Organic Chemistry |
| DOIs | |
| Publication status | Accepted/In press - 2017 |
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Keywords
- Diastereodivergent
- Henry reaction
- Manzacidin
- Tetrasubstituted carbon
- β,β-disubstituted β-amino alcohol
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons : Application to Total Synthesis of Manzacidins A and C. / Kudoh, Takayuki; Araki, Yuya; Miyoshi, Natsumi; Tanioka, Mizuho; Sakakura, Akira.
In: Asian Journal of Organic Chemistry, 2017.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons
T2 - Application to Total Synthesis of Manzacidins A and C
AU - Kudoh, Takayuki
AU - Araki, Yuya
AU - Miyoshi, Natsumi
AU - Tanioka, Mizuho
AU - Sakakura, Akira
PY - 2017
Y1 - 2017
N2 - β,β-Disubstituted β-amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration. Based on this methodology, a total synthesis of manzacidins A and C has been achieved.
AB - β,β-Disubstituted β-amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration. Based on this methodology, a total synthesis of manzacidins A and C has been achieved.
KW - Diastereodivergent
KW - Henry reaction
KW - Manzacidin
KW - Tetrasubstituted carbon
KW - β,β-disubstituted β-amino alcohol
UR - http://www.scopus.com/inward/record.url?scp=85032886295&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85032886295&partnerID=8YFLogxK
U2 - 10.1002/ajoc.201700568
DO - 10.1002/ajoc.201700568
M3 - Article
AN - SCOPUS:85032886295
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
SN - 2193-5807
ER -