α-allylated chiral thioxanones: Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence.

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

doi:10.1016/S0040-4039(00)92621-2

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 journal › Article

6 Scopus citations

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 language	English (US)
Pages (from-to)	335-338
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4039(00)92621-2
State	Published - Jan 14 1991
Externally published	Yes

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Tahir, S. H., Olmstead, M. M., & Kurth, M. J. (1991). α-allylated chiral thioxanones: Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence. Tetrahedron Letters, 32(3), 335-338. https://doi.org/10.1016/S0040-4039(00)92621-2

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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.",

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Access to Document

10.1016/S0040-4039(00)92621-2