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 journalArticlepeer-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 languageEnglish
Pages (from-to)1760-1763
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume6
Issue number12
DOIs
Publication statusPublished - 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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