LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

Wan Shin Kim, Claudio Aquino, Haruki Mizoguchi, Glenn C. Micalizio

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Abstract LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.

Original languageEnglish
Article number45698
Pages (from-to)3557-3559
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
Publication statusPublished - May 25 2015
Externally publishedYes

Fingerprint

Titanium
Oxidants
Oxidation
Organometallics
allyl alcohol
hydrindane

Keywords

  • Cascade reaction
  • Hydrindanes
  • Metallacycle-mediated cross-coupling
  • Oxidation
  • [2+2+2]

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade. / Kim, Wan Shin; Aquino, Claudio; Mizoguchi, Haruki; Micalizio, Glenn C.

In: Tetrahedron Letters, Vol. 56, No. 23, 45698, 25.05.2015, p. 3557-3559.

Research output: Contribution to journalArticle

Kim, Wan Shin ; Aquino, Claudio ; Mizoguchi, Haruki ; Micalizio, Glenn C. / LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 23. pp. 3557-3559.
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