Synlett

Stereoselective Intra-and Intermolecular [2+ 2] Photocycloaddition Reactions of 4-(2′-Aminoethyl) quinolones

S Brandes, P Selig, T Bach

Index: Brandes, Sebastian; Selig, Philipp; Bach, Thorsten Synlett, 2004 , # 14 p. 2588 - 2590

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Citation Number: 13

Abstract

Abstract The 4-(2′-aminoethyl) quinolones 6, 8 and 9 were prepared starting from 4-(2′- bromoethyl) quinolone (4) in two steps and overall yields of 56-93%. They underwent inter- and intramolecular [2+ 2] photocycloaddition reactions with an alkene to provide the cyclobutanes 1-3 in racemic form (61-89% yield). The photochemical reaction proceeded with very good chemo-, regio-and stereoselectivity. It was in one case (8b→ 2b) also ...