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Asymmetric Diels-Alder Reactions of Cyclopentadiene with N-Crotonoyl- and N-Acryloyl-4,4-Dimethyl-1,3-Oxazolidin-2-one, Mediated by Chiral Lewis Acids

✍ Scribed by Christian Chapuis; Janusz Jurczak

Publisher: John Wiley and Sons
Year: 1987
Tongue: German
Weight: 264 KB
Volume: 70
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19870700223

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✦ Synopsis

A crude, crystalline mixture 20a/20b (m.p. 102-103") was treated in analogous manner as that obtained from the reaction of cyclopentadiene with dienophile 2. 1,4-Di-O-tosyl-2,3-0-isopropylidene-~-threitol in y-pipecoline was refluxed for 3 h, and then the resulting product was hydrolyred to afford 14 (m.p. 69-70" from hexane, [M]E = -19.7" I C = 1.0, CCI,)) in 83% yield.

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