Asymmetric Diels??Alder Reaction of 1??Methoxybuta??1, 3??diene with (2R)??N??Glyoxyloylbornane??10, 2??sultam

…, C Chapuis, J Kozak, J Jurczak

Index: Bauer, Tomasz; Chapuis, Christian; Kozak, Janusz; Jurczak, Janusz Helvetica Chimica Acta, 1989 ,  vol. 72, p. 482 - 486

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Citation Number: 43

Abstract

Abstract Starting from sultam 1, the chiral dienophile (2R)-N-glyoxyloylbornane-10, 2-sultam (4) was readily prepared. Non-catalyzed atmospheric-and high-pressure as well as [Eu (fod) 3]-promoted [4+ 2] cycloadditions of 1-methoxy-buta-1, 3-diene (5) to chiral dienophile 4, leading with high asymmetric induction to 6-methoxy-3, 6-dihydro-2H-pyran-2-yl derivatives 6–9, are described. The extent and direction of asymmetric induction in these reactions ...