Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution

Matthew G. Unthank; Bahareh Tavassoli; Varinder K. Aggarwal

doi:10.1021/ol800318h

Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution

Matthew G. Unthank, Bahareh Tavassoli, Varinder K. Aggarwal

Research output: Contribution to journal › Article › peer-review

67 Citations (Scopus)

Abstract

(Chemical Equation Presented) Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.

Original language	English
Pages (from-to)	1501-1504
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	7
Early online date	13 Mar 2008
DOIs	https://doi.org/10.1021/ol800318h
Publication status	Published - 1 Apr 2008
Externally published	Yes

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10.1021/ol800318h

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abstract = "(Chemical Equation Presented) Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.",

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AU - Unthank, Matthew G.

AU - Tavassoli, Bahareh

AU - Aggarwal, Varinder K.

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N2 - (Chemical Equation Presented) Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.

AB - (Chemical Equation Presented) Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.

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Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution

Abstract

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