Tetrahedron

[2+ 2] Photocycloaddition of homochiral 2 (5H)-furanones to alkenes. First step for an efficient and diastereoselective synthesis of (+)-and (−)-grandisol

R Alibés, JL Bourdelande, J Font, A Gregori, T Parella

Index: Alibes; Bourdelande; Font; Gregori; Parella Tetrahedron, 1996 , vol. 52, # 4 p. 1267 - 1278

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Citation Number: 53

Abstract

The [2+ 2] photocycloaddition of homochiral 5-alkyl-2 (5H)-furanones to alkenes is studied in order to evaluate the influence of the stereogenie centre to induce facial diastereoselectivity. The major cycloadduct could be transformed, eventually, in (+)-grandisol, The existence of a charge-transfer complex between the furanone and electron rich substituted alkenes as well as the formation of a predominant conformation in 5-oxyalkylfuranones due to n-π ...