Synthesis 1990; 1990(7): 599-603
DOI: 10.1055/s-1990-26955
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Chiral Dienophiles Derived from Malic Acid: Synthesis of (Z)-(2S)-(tert-Butyl)-5-(ethoxycarbonylmethylene)-1,3-dioxolan-4-one and Its Diels-Alder Reaction with Cyclopentadiene

Georg Kneer* , Jochen Mattay, Gerhard Raabe, Carl Krüger, Jürgen Lauterwein
  • *Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Orléansring 23, D-4400 Münster, Federal Republic of Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

The synthesis of title chiral olefin 12 is described. Its structure is determined by X-ray analysis. The Diels-Alder reaction of 12 with cyclopentadiene exclusively yields the exo products with a face selectivity up to 95%.