Trimethylsilyl derivatives as final nucleophiles in the tandem sequence of an ArSCl-initiated AdE reaction resulting in the synthesis of polyfunctional compounds

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

“…The present communication describes the results of these studies. 10 As a model reaction a coupling of two methyl vinyl ether 1 units (VE-I and VE-II) was chosen which, as was assumed earlier, proceeds via formation of thiophanium intermediate 2 (Scheme 3).…”

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

“…

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]

…”

“…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]…”

“…‡ 8a: mp 85-87 °C (hexane-diethyl ether). 1 H NMR (CDCl 3 ) d: 1.10-2.04 (4m, 10H, 4CH 2 in ring, CH 2 in chain), 2.37 (m, 2H, CH 2 CH=), 2.42 (s, 3H, MePh), 2.83 (dd, 1H, CHSO 2 , 1 J 10.0 Hz, 2 J 14.4 Hz), 3.11 (s, 3H, MeO), 3.31 (s, 3H, MeO), 3.59 (dd, 1H, CHOMe, 1 J 5.1 Hz, 2 J 11.2 Hz), 5.16 (m, 2H, CH 2 =), 5.86 (m, 1H, CH=), 7.30 and 7.80 (2d, 4H arom , J 8.0 Hz). 13 suggest that the conformational rigidity of the bicyclic TPI-like intermediate derived from methoxycycloalkenes is the main factor that controls the steric outcome of the entire coupling.…”

“…1 H NMR (CDCl 3 ) d: 1.45-1.55 and 1.69-1.78 (2m, 8H, 4CH 2 in ring), 1.80 (dd, 1H, CH A , 1 J 2.4 Hz, 2 J 15.3 Hz), 2.14 (dd, 1H, CH B , 1 J 8.7 Hz, 2 J 15.3 Hz), 2.28 (s, 3H,…”