Coupling of Grignard Reagents with ArSCl Adducts of Vinyl Ethers as a Useful Option for Formation of Carbon-Carbon Bonds

Irina P. Smoliakova; Ron Caple; Jay W. Brenny; William A. Smit; Yury K. Kryschenko; Alexandr S. Shashkov; Oleg S. Chizhov; Miron Z. Krimer; Galina V. Morar; Yury B. Kalyan

doi:10.1055/s-1995-4934

Synlett 1995; 1995(3): 275-276
DOI: 10.1055/s-1995-4934

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Coupling of Grignard Reagents with ArSCl Adducts of Vinyl Ethers as a Useful Option for Formation of Carbon-Carbon Bonds

Irina P. Smoliakova¹ , Ron Caple, Jay W. Brenny, William A. Smit² , Yury K. Kryschenko, Alexandr S. Shashkov, Oleg S. Chizhov, Miron Z. Krimer, Galina V. Morar, Yury B. Kalyan

¹Department of Chemistry, University of Minnesota-Duluth, MN 55812, USA
²Zelinsky Institute of Organic Chemistry, Russian Academy of Science, pr. Lenina, 47, Moscow, Russia, 117913

Abstract

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Adducts formed upon Ad_E reaction of ArSCl with vinyl ethers were shown to be capable of reacting with Grignard reagents to give the corresponding β-arylthioalkylated products. In some cases it is preferable to run the reaction in the presence Li₂CuCl₄. A tandem sequence of (i) ArSCl addition to tri-O-benzyl-D-glucal followed by (ii) the coupling of the resulting adduct with a set of various Grignard reagents was elaborated as a fairly general and stereoselective pathway for the preparation of 2-arylthio-2-deoxy-β-C-glucosides.

Grignard reagent - vinyl ether - β-arylthioalkyl chloride - 2-deoxy-β-C-glucopyranoside - C-C bond formation

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