| dc.creator | De Faria A.R. | |
| dc.creator | Salvador E.L. | |
| dc.creator | Correia C.R.D. | |
| dc.date | 2002 | |
| dc.date | 2015-06-30T16:45:33Z | |
| dc.date | 2015-11-26T15:37:51Z | |
| dc.date | 2015-06-30T16:45:33Z | |
| dc.date | 2015-11-26T15:37:51Z | |
| dc.date.accessioned | 2018-03-28T22:46:17Z | |
| dc.date.available | 2018-03-28T22:46:17Z | |
| dc.identifier | | |
| dc.identifier | Journal Of Organic Chemistry. , v. 67, n. 11, p. 3651 - 3661, 2002. | |
| dc.identifier | 223263 | |
| dc.identifier | 10.1021/jo016189u | |
| dc.identifier | http://www.scopus.com/inward/record.url?eid=2-s2.0-0037204693&partnerID=40&md5=e1c3eef2a84c5afee3efcbde8e7a93b9 | |
| dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/101977 | |
| dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/101977 | |
| dc.identifier | 2-s2.0-0037204693 | |
| dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1263748 | |
| dc.description | The total systheses of two indolizidine skeletons and of the necine base (±)-platynecine were accomplished in a concise manner with good overall yields starting from a common five-membered endocyclic enecarbamate. These syntheses feature a (2 + 2)cycloaddition of the five-membered endocyclic enecarbamate 5 to alkykletenes that proceed in high yields and with high stereo-selectivity to provide an endo alkyl cycloadduct as the major or only product. The minor exo alkyl cycloadducts, which can be observed in some [2 +2]cycloadditions, seem to derive from the endo cycloadduct, the putative kinetic product, by epimerization. An unusual regioselectivity was observed for the Baeyer-Villiger oxidation is drastically reduced, leading to mixtures of regioselectivity of the Baeyer-Villager oxidation is drastically reduced, leading to mixtures of regioisomeric lactones in a ratio of ∼1.5 to 1. It is hypothesized that the steric strain built into the Criegee cyclobutane intermediate is the regioselectivity controlling factor in these oxidationas, overriding any stereoelectronic bias for ring expansion. A rationale for the mechanism of the [2 + 2]cycloaddition involving enecarbamates and ketenes is presented, which seems to involved the participation of an N-acyliminium-enolate intermediate. | |
| dc.description | 67 | |
| dc.description | 11 | |
| dc.description | 3651 | |
| dc.description | 3661 | |
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| dc.description | De Faria, A.R., Matos, C.R.R., Correia, C.R.D., (1993) Tetrahedron Lett., 34, p. 27 | |
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| dc.description | notenotenotenote | |
| dc.language | en | |
| dc.publisher | | |
| dc.relation | Journal of Organic Chemistry | |
| dc.rights | fechado | |
| dc.source | Scopus | |
| dc.title | Synthesis Of Indolizidines And Pyrrolizidines Through The [2 + 2]cycloaddition Of Five-membered Endocyclic Enecarbamates To Alkyl Ketenes. Unusual Regioselectivity Of Baeyer-villiger Ring Expansions Of Alkyl Aza-bicyclic Cyclobutanones | |
| dc.type | Artículos de revistas | |
