Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 17, Pages 3627-3648Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400502
Keywords
asymmetric catalysis; domino reactions; hydrogen bonds; organocatalysis; reaction mechanism
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Funding
- Spanish MINECO (FPI fellowship) [CTQ2011-22790]
- Spanish MINECO (Juan de la Cierva contract)
- Basque Government [IT328-10]
- UPV/EHU [UFI QOSYC 11/22, EHUA12/09]
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We have developed a procedure for the stereoselective and diastereodivergent synthesis of densely functionalised cyclohexanes containing four stereocentres through an asymmetric Michael-initiated ring closure (MIRC) cascade reaction employing hydrogen-bond catalysis, which is able to prepare adducts with different absolute configurations starting from the same starting materials. The overall process involves a highly diastereo- and enantioselective Michael/Henry cascade reaction between a wide range of nitroalkenes and alpha-nitro-delta-oxo esters, allowing access to different diastereoisomers of the final adduct by introducing subtle changes in the general (R,R)-configured bifunctional tertiary amine/squaramide catalyst structure. Moreover, this methodology is also amenable to a three-component one-pot procedure, leading to the formation of the same adducts with very good results directly from commercially available reagents, on a multigram scale, and employing a very low catalyst loading. Furthermore, a detailed experimental and computational study is described which shows the origin of the diastereodivergent behaviour of these structurally similar catalysts and the nature of the substrate-catalyst interaction.
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