Stereodivergent and stereoselective synthesis of cis-and trans-4-substituted prolinols

Junki Ando, Aoi Tazawa, Kohei Ishizawa, Minoru Tanaka, Hiroyoshi Takamura

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

- Stereoselective synthesis of 4-substituted prolinol derivatives has been developed. Thus, Suzuki-Miyaura cross-coupling of vinyl tritiate provided the common synthetic intermediates toward the stereodivergent synthesis of cis- and ira«s-4-substituted prolinols. These two kinds of target compounds were obtained by diastereoselective hydrogenation of the coupling products with Pd/C and Crabtree catalyst, respectively. In addition, the obtained 4-substituted prolinol was transformed to the corresponding proline derivative via oxidation in one step.

Original languageEnglish
Pages (from-to)188-199
Number of pages12
JournalHeterocycles
DOIs
Publication statusPublished - Jan 1 2019

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Derivatives
Hydrogenation
Proline
Oxidation
Catalysts
prolinol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Stereodivergent and stereoselective synthesis of cis-and trans-4-substituted prolinols. / Ando, Junki; Tazawa, Aoi; Ishizawa, Kohei; Tanaka, Minoru; Takamura, Hiroyoshi.

In: Heterocycles, 01.01.2019, p. 188-199.

Research output: Contribution to journalArticle

Ando, Junki ; Tazawa, Aoi ; Ishizawa, Kohei ; Tanaka, Minoru ; Takamura, Hiroyoshi. / Stereodivergent and stereoselective synthesis of cis-and trans-4-substituted prolinols. In: Heterocycles. 2019 ; pp. 188-199.
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