Four-component couplingvia a sequence of threeAd E reactions involving arenesulfenyl chloride, two alkyl vinyl ether units, and silicon-containing π-donors as a method for the synthesis of polyfunctional compounds

Abstract

A protocol for the synthesis of polyfunctional compounds by a Lewis acid initiated tandem sequence of three Ad E reactions of sulfur-containing electrophiles with two alkyl vinyl ether units and silicon containing n-donors is proposed.

Highly diastereocelective one-pot four-component coupling of p-TolSCI, 1-methoxycycloalkene, methyl vinyl ether and a carbon nucleophile leading to the synthesis of polyfunctional compounds

“…As a rule, in these cases, nearly 1:1 mixtures of diastereomers are formed, and this ratio was found to be only slightly affected by variations in the reaction parameters (the Lewis acid, the temperature, the solvent and the nature of the ArS substituent). 2,3 Here we demonstrate that the utilization of 1-methoxycycloalkenes as VE-I component affects dramatically the stereochemical outcome of the described reaction sequence, and highly stereoselective formation of a single diastereomer can be achieved.…”

“…These data taken together with the previously documented variability of the VE components used for the generation of the TPI-like intermediates well-attested to the generality and preparative promise of the developed procedure. 3 However, it was also found that this coupling, when executed with acyclic vinyl ethers employed as both VE-I and VE-II components, exhibits rather low diastereoselectivity at the newly created 1,3-chiral centres. As a rule, in these cases, nearly 1:1 mixtures of diastereomers are formed, and this ratio was found to be only slightly affected by variations in the reaction parameters (the Lewis acid, the temperature, the solvent and the nature of the ArS substituent).…”

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An one-pot TiCl 4 initiated assemblage of polyfunctional compounds via a sequential coupling of p-TolSCl, 1-methoxycycloalkene, methyl vinyl ether and Sn-or Si-capped carbon nucleophile is shown to proceed with high diastereoselectivity at all newly created chiral centres.The sequence of three kinetically independent intermolecular Ad E reactions mediated by sulfur-stabilized reagents and intermediates has been recently developed as a versatile method for the one-pot synthesis of polyfunctional compounds from simple precursors in accordance with Scheme 1. [1][2][3]

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“…The sequence of three kinetically independent intermolecular Ad E reactions mediated by sulfur-stabilized reagents and intermediates has been recently developed as a versatile method for the one-pot synthesis of polyfunctional compounds from simple precursors in accordance with Scheme 1. [1][2][3]…”

μ-Alkyne dicobalt hexacarbonyl complexes of conjugated enynes as substrates in the arylthio-mediated stepwise AdE reactions

“…3,4 This approach was successfully applied to a number of three-and four-component couplings outlined in Scheme 1 as options A and B, respectively. [3][4][5] The formation of episulfonium ion (ESI) and thiophanium ion (TPI) intermediates in these couplings was well-substantiated by the observed pattern of their reactivity and in several cases was also unequivocally proven by the results of NMR and X-ray studies of the isolated salts. 6,7 Option A was shown to be applicable to a wide set of structurally diverse non-functionalised alkenes, as well as to 1-alkoxyalkenes.…”