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- Title
Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence.
- Authors
Reddy, Reddy Rajasekhar; Gudup, Satish Sonbarao; Ghorai, Prasanta
- Abstract
An unprecedented enantioselective oxa-Michael reaction of α-tertiary alcohols using cinchona-alkaloid-based chiral bifunctional squaramide catalysts is reported. An oxidative dearomatization of phenol followed by an enantioselective oxa-Michael addition sequence provided a broad array of chiral sterically hindered tetrahydrofurans and tetrahydropyrans attached to a cyclohexadienone moiety in spiro fashion. In general, good yields and excellent enantioselectivities (up to 99 %) were observed. The chiral oxo-cycles obtained have easily been transformed into chromans without disturbing the enantioselectivity.
- Subjects
ORGANOCATALYSIS; ENANTIOSELECTIVE catalysis; CYCLOHEXADIENONES; ETHERS; MICHAEL reaction
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 48, p15339
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201607039