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Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters

✍ Scribed by Michal Achmatowicz; Christian Chapuis; Piotr Rzepecki; Janusz Jurczak

Publisher: John Wiley and Sons
Year: 1999
Tongue: German
Weight: 134 KB
Volume: 82
Category: Article
ISSN: 0018-019X
DOI: 10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p

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✦ Synopsis

The [4 2] cycloaddition of cyclopentadiene to the (2R )-bornane-10,2-sultam derivative (À)-1b of fumaric monomethyl ester proceeds with high endo and p-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl 4 . The major diastereoisomer endo-(2R,3R )-2b, isolated in 87% yield by crystallization, was subjected to Xray crystal-structure analysis. Steric influence of ethyl-and benzyl-ester analogues (À)-1c and (À)-1d, respectively, is also reported.

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