A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines with allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers of unprecedented spirocyclic oxindoles, bearing a 4-methyleneazetidine ring at the spiro junction. The versatility of the method is fully demonstrated by further transformations including the conversion to relevant spirocyclic oxindolo-[small beta]-lactams.
Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction / G. Rainoldi, M. Faltracco, L. Lo Presti, A. Silvani, G. Lesma. - In: CHEMICAL COMMUNICATIONS. - ISSN 1364-548X. - 52:77(2016 Aug 26), pp. 11575-11578. [10.1039/C6CC05838H]
Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction
G. RainoldiPrimo
;L. Lo Presti;A. Silvani
;G. LesmaUltimo
2016
Abstract
A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines with allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers of unprecedented spirocyclic oxindoles, bearing a 4-methyleneazetidine ring at the spiro junction. The versatility of the method is fully demonstrated by further transformations including the conversion to relevant spirocyclic oxindolo-[small beta]-lactams.File | Dimensione | Formato | |
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Rainoldi_Faltracco_Lo-Presti_Silvani_Lesma_Chem_Comm_2016_52_11575-11578.pdf
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Paper_Silvani_Azetidine_CHEMCOMM_REVISED.pdf
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