Abstract
A bifunctional squaramide-catalyzed sulfa-Michael/aldol cascade reaction between benzylidenechroman-4-ones and 1,4-dithiane-2,5-diol with a low catalyst loading has been developed. This reaction constitutes a facile asymmetric synthesis of chiral spirocyclic tetrahydrothiophene chromanone derivatives with three contiguous stereocenters in high to excellent yields (up to 99%) and with high enantioselectivities (up to 92% ee). Additionally, a remarkable temperature effect on reaction efficiency was observed and gram-scale syntheses were found to proceed smoothly with the same efficiency as smaller scale reactions.
Original language | English |
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Pages (from-to) | 7850-7858 |
Number of pages | 9 |
Journal | European Journal of Organic Chemistry |
Volume | 2014 |
Issue number | 35 |
DOIs | |
Publication status | Published - 28 Oct 2014 |
Keywords
- Aldol reactions
- Asymmetric synthesis
- Cascade reaction
- Michael addition
- Organocatalysis
- Sulfur heterocycles