Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 27, Pages 7723-7727Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511165
Keywords
asymmetric synthesis; heterocycles; Michael addition; organocatalysis; peroxides
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Funding
- CSIR, New Delhi
- IISER Bhopal
- UGC, New Delhi, India
- CSIR, New Delhi, India
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An unprecedented enantioselective peroxyhemiacetalization/oxa-Michael addition cascade of ortho-formyl homochalcones has been developed using cinchona-alkaloid-based chiral bifunctional organocatalysts to provide cisconfigured exo-peroxyacetals, a new class of organic peroxide, in good yields with excellent enantio-and diastereoselectivities. The resulting cis-configured exo-peroxyacetals were converted into the corresponding trans-configured peroxyacetals without affecting the enantioselectivity. Furthermore, the displacement of the peroxide moiety of exo-peroxyacetals with various nucleophiles has been demonstrated to afford 1,3-disubstituted isochromans with high diastereoselectivities and excellent enantioselectivities.
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