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
Journal	Asian Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ajoc.201700568
Publication status	Accepted/In press - 2017

Keywords

Diastereodivergent
Henry reaction
Manzacidin
Tetrasubstituted carbon
β,β-disubstituted β-amino alcohol

ASJC Scopus subject areas

Organic Chemistry

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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; Tanioka, Mizuho; Sakakura, Akira.

In: Asian Journal of Organic Chemistry, 2017.

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

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AU - Sakakura, Akira

PY - 2017

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