Subscribe to RSS
DOI: 10.1055/s-0036-1591838
Enantioselective Construction and Transformations of Polyfunctionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines
We are grateful for financial support from the National Natural Science Foundation of China (21272214).Publication History
Received: 18 September 2017
Accepted after revision: 29 October 2017
Publication Date:
11 December 2017 (online)


Abstract
We developed an enantioselective organocascade Michael/Henry reaction in the presence of a bifunctional organocatalyst to construct chiral polyfunctionalized 3,4-dihydro-2H-thiopyrano[2,3-b]quinolines. The resulting optically active products with three contiguous stereocenters, one quaternary and two tertiary, were obtained in moderate to good yields and with good to excellent enantioselectivities. Remarkably, the resulting products were readily converted into polyfunctionalized optically active furo[2′,3′:4,5]thiopyrano[2,3-b]quinoline, 3,4-dihydro-2H-thiopyrano[2,3-b]quinoline 1-oxide and 2,3-dihydro-4H-thiopyrano[2,3-b]quinolin-4-one derivatives.
Key words
Domino reaction - Michael addition - Henry reaction - thiopyranoquinolines - polyheterocycles - cascade reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591838.
- Supporting Information