α-allylated chiral thioxanones

Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence.

S. Hasan Tahir, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Diastereoselective S-allylation of thioxanone 6 and subsequent ylid formation/[2,3]-sigmatropic rearrangement delivers excellent Cα-induction. Non-stereospecific Cβ-induction results from scrambling of olefin geometry in the S-allylation step.

Original languageEnglish (US)
Pages (from-to)335-338
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number3
DOIs
StatePublished - Jan 14 1991
Externally publishedYes

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Allylation
Alkylation
Alkenes
Geometry

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

α-allylated chiral thioxanones : Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence. / Tahir, S. Hasan; Olmstead, Marilyn M.; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 32, No. 3, 14.01.1991, p. 335-338.

Research output: Contribution to journalArticle

Tahir, S. Hasan ; Olmstead, Marilyn M. ; Kurth, Mark J. / α-allylated chiral thioxanones : Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 3. pp. 335-338.
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