Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C

Takayuki Kudoh; Yuya Araki; Natsumi Miyoshi; Mizuho Tanioka; Akira Sakakura

doi:10.1002/ajoc.201700568

Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C

Takayuki Kudoh, Yuya Araki, Natsumi Miyoshi, Mizuho Tanioka, Akira Sakakura

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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
Pages (from-to)	1760-1763
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	6
Issue number	12
DOIs	https://doi.org/10.1002/ajoc.201700568
Publication status	Published - Dec 2017

Keywords

Henry reaction
diastereodivergent
manzacidin
tetrasubstituted carbon
β,β-disubstituted β-amino alcohol

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201700568

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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 et al.

In: Asian Journal of Organic Chemistry, Vol. 6, No. 12, 12.2017, p. 1760-1763.

Research output: Contribution to journal › Article › peer-review

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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.",

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note = "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. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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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. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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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.

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Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C

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Keywords

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