Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Dynamic Kinetic Spiroketalization/Oxa-Michael Addition Cascade of Alkoxyboronates and Peroxyacetals: Enantio- and Diastereoselective Synthesis of Benzannulated Spiroketals

Dynamic Kinetic Spiroketalization/Oxa-Michael Addition Cascade of Alkoxyboronates and Peroxyacetals: Enantio- and Diastereoselective Synthesis of Benzannulated Spiroketals
Abhisek Midya, Prasanta Ghorai, Sanjay Maity
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. The first catalytic asymmetric syntheses of isobenzofuran-based benzannulated spiroketals and exo-peroxy-benzannulated spiroketals have been developed. A series of valuable chiral benzannulated spiroketals were obtained in high yields, high diastereoselectivities, and outstanding enantioselectivities (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701291

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