Abstract
A unified dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of an aromatic ketone tethered to an alkoxyboronate and an enone moiety has been developed using cinchona alkaloid based amino-thiourea/squaramide organocatalysts to provide isobenzofuran-based benzannulated spiroketals with high diastereoselectivities and excellent enantioselectivities. Further, a dynamic kinetic peroxy-hemiacetalization/dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of the above substrates provides the corresponding exo-peroxy-benzannulated spiroketals with outstanding enantio- and diastereoselectivities.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 11216-11220 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 23 |
| Issue number | 47 |
| DOIs | |
| State | Published - Aug 22 2017 |
| Externally published | Yes |
Bibliographical note
Publisher Copyright:© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- asymmetric synthesis
- benzannulated spiroketals
- organocatalysis
- oxa-Michael addition
- peroxy spiroketals
- spiroketals