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Regioselective and Asymmetric Diels−Alder Reaction of 1- and 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated Chiral Oxazaborolidine

✍ Scribed by Payette, Joshua N.; Yamamoto, Hisashi

Book ID: 120247992
Publisher: American Chemical Society
Year: 2007
Tongue: English
Weight: 53 KB
Volume: 129
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja0735958

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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 1