Cis-homo addition-1,4 thiophile d'organomagnesiens avec des composes thiocarbonyles comportant un groupe carbonyle en β: Synthese stereoselective d'alcoylthio-2 et de bis (alcoylthio)-2,2 cyclopropanols |
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| Authors: | J Masson P Metzner J Vialle |
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| Institution: | Laboratoire de Chimie des Composés Thioorganiques, ERA CNRS 391, Université de Caen, 14032 Caen Cédex, France |
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| Abstract: | Aliphatic Grignard reagents react stereoselectively with β thioxo carbonyl compounds to give substituted cis 2-alkylthio or 2,2-bis (alkylthio) cyclopropanols with good yields. Two types of non-enethiolisable thiocarbonyl compounds of formulae MeCOC(Me)2CSR undergo this reaction a thioketone (R = Me) and a number of dithioesters (R = SMe, SEt, S iso Pr). The cis configuration of cyclopropanols has been assigned by 1H NMR-Eu(fod)3. The cyclopropane ring closure is a concerted cis-1,4-homo addition. |
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