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Asymmetric induction in Diels-Alder reactions to acrylates derived from chiral sec-alcohols. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; Mark Kurth; Daniel Reichlin; Christian Chapuis; Martin Mohnhaupt; Frank Moffatt

Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 328 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640841

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✦ Synopsis

Abstract

Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl~4~‐promoted Diels‐Alder addition to cyclopentadiene (Scheme 3, Table) giving in a predictable manner either the (2__R__)‐ or the (2__S__)‐adducts III with 63 to 88% asymmetric induction.

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Starting from (R)-(+)-and from (S)-(-)-camphor the chiral alcohols 1: 2 and 3 have been prepared; their acrylates II underwent TiCl,(OR),-promoted Diels-Alder additTons to cyclopentadiene giving efficiently in a predictable manner either the (2R)-or the (2S)-adducts III with up to virtually quantita