A metal-free stereoselective catalytic addition of in situ generated dienamine to β-nitroacrylates has been developed. Starting from simple α,β unsaturated ketones, highly functionalized chiral β-nitrocyclohexanecarboxylic esters were obtained in a single step, in good yields and up to 98% ee. By an unprecedented mechanistic pathway, starting from the synthetically readily available E-nitroacrylate, the present methodology allowed us to obtain as major product the isomer bearing a cis relative disposition between the nitro and the ester groups, which is not accessible via a classical Diels-Alder reaction.
Stereoselective synthesis of functionalized chiral 2- nitrocyclohexanecarboxylic esters via catalytic dienamine addition to β-substituted β-nitroacrylates / E. Massolo, M. Benaglia, R. Annunziata, A. Palmieri, G. Celentano, A. Forni. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 356:2-3(2014), pp. 493-500. [10.1002/adsc.201301074]
Stereoselective synthesis of functionalized chiral 2- nitrocyclohexanecarboxylic esters via catalytic dienamine addition to β-substituted β-nitroacrylates
E. MassoloPrimo
;M. Benaglia
;R. Annunziata;G. CelentanoPenultimo
;A. ForniUltimo
2014
Abstract
A metal-free stereoselective catalytic addition of in situ generated dienamine to β-nitroacrylates has been developed. Starting from simple α,β unsaturated ketones, highly functionalized chiral β-nitrocyclohexanecarboxylic esters were obtained in a single step, in good yields and up to 98% ee. By an unprecedented mechanistic pathway, starting from the synthetically readily available E-nitroacrylate, the present methodology allowed us to obtain as major product the isomer bearing a cis relative disposition between the nitro and the ester groups, which is not accessible via a classical Diels-Alder reaction.File | Dimensione | Formato | |
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