α'-Hydroxy enones as achiral templates for Lewis acid-catalyzed enantioselective diels-alder reactions

…, M Oiarbide, JM García, A González…

Index: Palomo, Claudio; Oiarbide, Mikel; Garcia, Jesus M.; Gonzalez, Alberto; Arceo, Elena Journal of the American Chemical Society, 2003 , vol. 125, # 46 p. 13942 - 13943

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Citation Number: 50

Abstract

α'-Hydroxy enones react with dienes in the presence of (S, S)-[Cu (tBu-box)](OTf) 2 or (S, S)- [Cu (tBu-box)](SbF6) 2 (2 to 10 mol%) to afford the corresponding Diels-Alder adducts in high yield and selectivity. Isomeric ratios (regioselectivity, endo/exo or cis/trans) of up to> 99: 1 and ee values of up to> 99% are obtained. Significantly, difficult dienes such as isoprene, 2, 3-dimethyl butadiene and piperylene behave satisfactorily. Subsequent oxidative ...