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- Title
Highly Enantioselective Intramolecular 1,3-Dipolar Cycloaddition: A Route to Piperidino-Pyrrolizidines.
- Authors
Vidadala, Srinivasa Rao; Golz, Christopher; Strohmann, Carsten; Daniliuc, Constantin ‐ G.; Waldmann, Herbert
- Abstract
Enantioselective catalytic intermolecular 1,3-dipolar cycloadditions are powerful methods for the synthesis of heterocycles. In contrast, intramolecular enantioselective 1,3-dipolar cycloadditions are virtually unexplored. A highly enantioselective synthesis of natural-product-inspired pyrrolidino-piperidines by means of an intramolecular 1,3-dipolar cycloaddition with azomethine ylides is now reported. The method has a wide scope and yields the desired cycloadducts with four tertiary stereogenic centers with up to 99 % ee. Combining the enantioselective catalytic intramolecular 1,3-dipolar cycloaddition with a subsequent diastereoselective intermolecular 1,3-dipolar cycloaddition yielded complex piperidino-pyrrolizidines with very high stereoselectivity in a one-pot tandem reaction.
- Subjects
PYRROLIZIDINES; PYRROLES; ALKALOIDS; MONOCROTALINE; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 2, p661
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201409942