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

✍ Scribed by Tomasz Bauer; Christian Chapuis; Janusz Kozak; Janusz Jurczak

Publisher: John Wiley and Sons
Year: 1989
Tongue: German
Weight: 240 KB
Volume: 72
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19890720310

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✦ Synopsis

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Starting from sultam 1, the chiral dienophile (2R)-N-glyoxyloylbornane-lO,2-sultam (4) was readily prepared.

Non-catalyzed atmospheric-and high-pressure as well as [Eu(fod),]-promoted [4 + 21 cycloadditions of l-methoxybuta-l,3-diene (5) to chiral dienophile 4, leading with high asymmetric induction to 6-methoxy-3,6-dihydro-2Hpyran-2-yl derivatives 6 9 , are described. The extent and direction of asymmetric induction in these reactions were established by 'H-NMR analysis and chemical correlation, respectively. Stereochemical models for both non-catalyzed and [E~(fod)~]-promoted reactions are proposed.

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