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 › peer-review

7 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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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

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.",

author = "Tahir, {S. Hasan} and Olmstead, {Marilyn M.} and Kurth, {Mark J.}",

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T1 - α-allylated chiral thioxanones

T2 - Diastereoselective preparation by an S-alkylation/[2,3]-sigmatropic rearrangement sequence.

AU - Tahir, S. Hasan

AU - Olmstead, Marilyn M.

AU - Kurth, Mark J.

PY - 1991/1/14

Y1 - 1991/1/14

N2 - 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.

AB - 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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U2 - 10.1016/S0040-4039(00)92621-2

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M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

ASJC Scopus subject areas

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