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

5 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

Access to Document

10.1002/ajoc.201700568

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, Vol. 6, No. 12, 12.2017, p. 1760-1763.

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

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

author = "Takayuki Kudoh and Yuya Araki and Natsumi Miyoshi and Mizuho Tanioka and Akira Sakakura",

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",

year = "2017",

month = dec,

doi = "10.1002/ajoc.201700568",

language = "English",

volume = "6",

pages = "1760--1763",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "12",

}

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

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

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

VL - 6

SP - 1760

EP - 1763

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 12

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this