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Diels–Alder reactions of phenylglycinol-derived bicyclic lactams. Enantiodivergent synthesis of cis-hydroisoquinolines

✍ Scribed by Núria Casamitjana; Mercedes Amat; Núria Llor; Marçal Carreras; Xavier Pujol; M. Montserrat Fernández; Virgina López; Elies Molins; Carles Miravitlles; Joan Bosch

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 302 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00368-9

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✦ Synopsis

The diastereomeric phenylglycinol-derived unsaturated d-lactams trans-3 and cis-3 react with dienes with exo facial diastereoselectivity to give the corresponding tricyclic adducts, which were ultimately converted to enantiomeric cis-hydroisoquinolines.

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