Asymmetric bias generated by protected vicinal diol controller and its application to asymmetric nitrone-olefin cycloaddition reactions

Seiki Saito, Teruhiko Ishikawa

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

In order to achieve the diastereo-differentiation of π-faces, we have developed the protected vicinal-diol controller. The striking successes in stereocontrol of diverse organic reactions have been recorded for which the diastereofacial bias constructed by such diol controller should be responsible. We refer to this topological situation as "outside-inside bias". This review summarizes the application of this concept to nitrone-olefin [3+2] cycloaddition reactions which resulted in considerable successes in stereocontrol again, and covers three topics, (1) the substrate-controlled intermolecular asymmetric cycloaddition reactions, (2) intramolecular 1,3-dipolar cycloaddition reactions of chiral alkenylnitrones, and (3) the synthesis of cyclic chiral nitrones and its intermolecular asymmetric cycloaddition reactions with various olefins. The role of the vicinal diol controller in these processes has been delineated.

Original languageEnglish
Pages (from-to)86-95
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume56
Issue number2
Publication statusPublished - Feb 1998

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Cycloaddition
Alkenes
Controllers
nitrones
Substrates

Keywords

  • Alkenyl nitrones
  • Cyclic chiral nitrone
  • Diastereofacial bias
  • Diastereoselection
  • Intermolecular asymmetric cycloaddition reaction
  • Intramolecular asymmetric cycloaddition reaction
  • Nitrone-olefin [3+2] cycloaddition
  • Vicinal diol controller

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "In order to achieve the diastereo-differentiation of π-faces, we have developed the protected vicinal-diol controller. The striking successes in stereocontrol of diverse organic reactions have been recorded for which the diastereofacial bias constructed by such diol controller should be responsible. We refer to this topological situation as {"}outside-inside bias{"}. This review summarizes the application of this concept to nitrone-olefin [3+2] cycloaddition reactions which resulted in considerable successes in stereocontrol again, and covers three topics, (1) the substrate-controlled intermolecular asymmetric cycloaddition reactions, (2) intramolecular 1,3-dipolar cycloaddition reactions of chiral alkenylnitrones, and (3) the synthesis of cyclic chiral nitrones and its intermolecular asymmetric cycloaddition reactions with various olefins. The role of the vicinal diol controller in these processes has been delineated.",
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AU - Ishikawa, Teruhiko

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