Abstract
An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.
Highlights
An unprecedented stereoselective organocatalytic one-pot 1,4-/ 1,6-/1,2-addition sequence between b-dicarbonyl compounds, b-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed
The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities
Over the last ten years, asymmetric organocatalytic cascade reactions have emerged as a powerful strategy for the synthesis of complex molecules bearing multiple stereogenic centers in a highly stereocontrolled fashion.[1]
Summary
An unprecedented stereoselective organocatalytic one-pot 1,4-/ 1,6-/1,2-addition sequence between b-dicarbonyl compounds, b-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.
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