Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 38, Pages 12133-12143Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402965
Keywords
borono-Mannich reaction; carbohydrates; Diels-Alder reaction; domino reactions; metathesis
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Funding
- ICSN-CNRS
- Institut Universitaire de France (IUF)
- CHARM3AT program
- LERMIT Labex program
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One-step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono-Mannich) and Diels-Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is applicable to a broad range of substrates, including free sugars, and holds significant potential to efficiently and stereoselectively build new heterocyclic structures. This easy and fast entry to functionalized polycyclic compounds can be pursued by further transformations, for example, additional ring closure by a cross-metathesis/Michael addition domino sequence.
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