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
N1 - Funding Information:
This project was financially supported in part by JSPS KAKENHI (26410120). The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University for the NMR and HRMS measurements.
PY - 2017/12
Y1 - 2017/12
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 - Henry reaction
KW - diastereodivergent
KW - manzacidin
KW - tetrasubstituted carbon
KW - β,β-disubstituted β-amino alcohol
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U2 - 10.1002/ajoc.201700568
DO - 10.1002/ajoc.201700568
M3 - Article
AN - SCOPUS:85032886295
VL - 6
SP - 1760
EP - 1763
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
SN - 2193-5807
IS - 12
ER -