Asymmetric Michael reaction promoted by chiral thiazolidine-thiourea catalyst
In this work, we report the synthesis and characterization of three new thiazolidine- and thiourea-based chiral organocatalysts. These compounds were successfully applied in asymmetric Michael addition reactions between different ketones and nitrostyrenes leading to products in up to 85% yield, >96:4 r.d. and 97% e.e. Computational studies were used to better visualize the proposed transition state and explain the observed stereoselectivities. One of the new catalysts was also successfully applied in an aldol addition between cyclohexanone an p-nitrobenzaldehyde leading to product in 80% yield, >96:4 d.r. and 80% e.e.
da Silva, Tiago Lima,Rambo, Raoni Scheibler,Jacoby, Caroline Gross,Schneider, Paulo Henrique
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(2019/12/27)
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