Synlett

A novel method for the stereoselective synthesis of tetralins and indanes

Z Appelbe, M Casey, CM Keaveney, CJ Kelly

Index: Appelbe, Zelda; Casey, Mike; Keaveney, Claire M.; Kelly, Cornelius J. Synlett, 2002 , # 9 p. 1404 - 1408

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Citation Number: 4

Abstract

Abstract Heavily-substituted 1-aryltetralins and 1-arylindanes were prepared in a highly stereoselective manner using a two-step sequence. Addition of t-butyl benzyl sulfoxides to unsaturated carbonyl compounds gave conjugate adducts with high diastereoselectivity. Treatment of the adducts with SnCl 4 generated benzyl carbocations which reacted intramolecularly with suitably-positioned aromatic rings to give tetralins and indanes, ...