Preparation of a Chiral Building Block by an Organocatalytic Asymmetric Intramolecular Michael Reaction

Yusuke Sato, Yosuke Hosoya, Ikumi Kobayashi, Kyohei Adachi, Masahisa Nakada

Research output: Contribution to journalArticle

Abstract

The preparation of a chiral building block, including a stereodiad consisting of two tertiary stereogenic centers, by a highly enantioselective organocatalytic intramolecular Michael reaction is described. The use of a chiral secondary-amine-bearing thiourea substituted with a para-nitrophenyl group in the presence of benzoic acid is key to preparing the chiral building block in high yield and excellent enantioselectivity. The prepared chiral building block has both aldehyde and nitro groups, allowing a variety of functional-group transformations necessary for the total synthesis of atisane-type terpenoids.

Original languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusPublished - 2019 Jan 1

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Bearings (structural)
Thiourea
Benzoic Acid
Enantioselectivity
Terpenes
Aldehydes
Functional groups
Amines
4-nitrophenyl

Keywords

  • enantioselectivity
  • intramolecular cyclization
  • Michael reaction
  • nitroalkene
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of a Chiral Building Block by an Organocatalytic Asymmetric Intramolecular Michael Reaction. / Sato, Yusuke; Hosoya, Yosuke; Kobayashi, Ikumi; Adachi, Kyohei; Nakada, Masahisa.

In: Asian Journal of Organic Chemistry, 01.01.2019.

Research output: Contribution to journalArticle

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