Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic OxindolesShow others and affiliations
2015 (English)In: ACS Catalysis, E-ISSN 2155-5435, Vol. 5, no 2, p. 1266-1272Article in journal (Refereed) Published
Abstract [en]
The highly enantioselective (up to >99.5:0.5 er) synthesis of polysubstituted spirocyclic oxindoles with four new contiguous stereocenters, including the spiro all-carbon quaternary center, is disclosed. It is accomplished by the highly stereoselective control of a dynamic conjugate/intramolecular allylic alkylation relay sequence based on the synergistic cooperation of metal and chiral amine catalysts in which the careful selection of organic Nand, metal complex, and chiral amine is essential. The intermolecular C-C bond-forming step occurred only when both the metal and chiral amine catalysts were present.
Place, publisher, year, edition, pages
2015. Vol. 5, no 2, p. 1266-1272
Keywords [en]
all-carbon quaternary stereocenter, asymmetric cocatalysis, dynamic transformations, polysubstituted, spirocyclic oxindoles, α, β-unsaturated aldehydes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-24590DOI: 10.1021/cs501975uISI: 000349275300086Scopus ID: 2-s2.0-84922713231OAI: oai:DiVA.org:miun-24590DiVA, id: diva2:795786
2015-03-172015-03-172025-09-25Bibliographically approved