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Polymer-supported chiral diol as ligand of Ti(IV) for enantioselective Diels-Alder reaction

✍ Scribed by José Irurre; Anna Fernández-Serrat; Francesc Rosanas

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 171 KB
Volume: 9
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(1997)9:2<191::aid-chir21>3.0.co;2-h

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✦ Synopsis

The synthesis of the first polymer-supported TADDOL is reported. Its efficiency as chiral ligand of Ti(IV) was studied in the Diels-Alder cycloaddition of cyclopentadiene to 3-crotonoyl-1,3-oxazolidin-2-one, and was superior to that observed for its homogeneous equivalent, (4R,5R)-␣,␣,␣Ј,␣Ј-2-pentaphenyl-4,5-dimethanol-1,3dioxolane. Recycling of the heterogeneous Ti(IV)-TADDOLate was also studied, being the most suitable method for the repreparation of the catalyst from the ligand after use.

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