2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Jun ichi Yoshida, Kenichiro Itami, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

Original languageEnglish
Pages (from-to)3403-3406
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number17
DOIs
Publication statusPublished - Apr 23 1999
Externally publishedYes

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Acids
Hydrosilylation
Oxidation
Alkenes
Recovery
Molecules

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis. / Yoshida, Jun ichi; Itami, Kenichiro; Mitsudo, Koichi; Suga, Seiji.

In: Tetrahedron Letters, Vol. 40, No. 17, 23.04.1999, p. 3403-3406.

Research output: Contribution to journalArticle

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