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 journalArticlepeer-review

66 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 languageEnglish
Pages (from-to)1501-1504
Number of pages4
JournalOrganic Letters
Volume10
Issue number7
Early online date13 Mar 2008
DOIs
Publication statusPublished - 1 Apr 2008
Externally publishedYes

Fingerprint

Dive into the research topics of 'Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution'. Together they form a unique fingerprint.

Cite this