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

3 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 languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2017

Fingerprint

Amino Alcohols
Nitrogen
Carbon

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

Kudoh, T, Araki, Y, Miyoshi, N, Tanioka, M & Sakakura, A 2017, 'Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C', Asian Journal of Organic Chemistry. https://doi.org/10.1002/ajoc.201700568
Kudoh T, Araki Y, Miyoshi N, Tanioka M, Sakakura A. Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C. Asian Journal of Organic Chemistry. 2017. https://doi.org/10.1002/ajoc.201700568
Kudoh, Takayuki ; Araki, Yuya ; Miyoshi, Natsumi ; Tanioka, Mizuho ; Sakakura, Akira. / Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons : Application to Total Synthesis of Manzacidins A and C. In: Asian Journal of Organic Chemistry. 2017.
@article{7cf089fa4e0244d3bd30065ea5466f3c,
title = "Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C",
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.",
keywords = "Diastereodivergent, Henry reaction, Manzacidin, Tetrasubstituted carbon, β,β-disubstituted β-amino alcohol",
author = "Takayuki Kudoh and Yuya Araki and Natsumi Miyoshi and Mizuho Tanioka and Akira Sakakura",
year = "2017",
doi = "10.1002/ajoc.201700568",
language = "English",
journal = "Asian Journal of Organic Chemistry",
issn = "2193-5807",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

}

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

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

ER -

Access to Document