Diastereoselective intramolecular SmI 2–H2O–amine mediated couplings

A Dahlén, A Petersson, G Hilmersson

Index: Dahlen, Anders; Petersson, Annika; Hilmersson, Goeran Organic and Biomolecular Chemistry, 2003 , vol. 1, # 14 p. 2423 - 2426

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Citation Number: 26

Abstract

First 1-allyloxy-2-iodobenzene (1) was synthesised to establish whether this type of coupling was achievable at all. Mixing of SmI 2 , Et 3 N, 1 followed by H 2 O gave an almost instantaneous reaction and the product was isolated and characterised by 1 H-NMR, COSY and GC/MS. We found that the reaction yielded only one product, the coupled product 3-methyl-2,3-dihydrobenzofuran (1a). Analogue substrates containing longer alkyl chains were also investigated for ...