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- Title
Asymmetric induction in Diels- Alder reactions to acrylates derived from chiral sec-alcohols. Preliminary communication.
- Authors
Oppolzer, Wolfgang; Kurth, Mark; Reichlin, Daniel; Chapuis, Christian; Mohnhaupt, Martin; Moffatt, Frank
- 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 TiCl4-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.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 8, p2802
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640841