Publication
Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole
| dc.contributor.author | Gilchrist, Thomas L. | |
| dc.contributor.author | Lemos, A. | |
| dc.contributor.author | Ottaway, Carol J. | |
| dc.date.accessioned | 2012-03-09T16:00:19Z | |
| dc.date.available | 2012-03-09T16:00:19Z | |
| dc.date.issued | 1997 | |
| dc.date.updated | 2012-02-27T17:44:12Z | |
| dc.description.abstract | The azabicyclo[3.2.0]heptan-7-ones 4, 10, 16 and 24 have been prepared from pyrrole. The same general approach has been used for all these derivatives; namely, substitution of pyrrole at the 2- and 5-carbon atoms, catalytic hydrogenation to produce pyrrolidine-2-acetic acid derivatives, and cyclisation using tris(1,3-dihydro-2-oxobenzoxazol-3-yl)phosphine oxide 6. The catalytic hydrogenation of 2,5-disubstituted pyrroles gives only the corresponding cis-2,5-disubstituted pyrrolidines. The hydrogenation proceeds more easily when the nitrogen atom bears a tert-butoxycarbonyl substituent. The N-tert-butoxycarbonylpyrroles 8 and 21 bearing an á-substituent in the acetate side chain were hydrogenated with a high degree of facial stereoselectivity. This allowed the 6-phthalimidoazabicyclo- [3.2.0]heptan-7-one 24 to be isolated as a single diastereoisomer. The X-ray crystal structure of a precursor, the triester, 22a, has been obtained. | por |
| dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 20, 3005-3012, 1997. | por |
| dc.identifier.issn | 0300922X | |
| dc.identifier.other | AUT: ALE01411; | |
| dc.identifier.uri | http://hdl.handle.net/10400.1/935 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.subject | Heterocycles | por |
| dc.subject | Diels-Alder | por |
| dc.title | Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole | por |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| person.familyName | Lemos | |
| person.givenName | Americo | |
| person.identifier.ciencia-id | A81D-6DC7-31E4 | |
| person.identifier.orcid | 0000-0001-9588-4555 | |
| person.identifier.rid | B-4892-2008 | |
| person.identifier.scopus-author-id | 11139694000 | |
| rcaap.rights | openAccess | por |
| rcaap.type | article | por |
| relation.isAuthorOfPublication | 70dfe028-027a-4dec-b6e3-1a49c9be9e60 | |
| relation.isAuthorOfPublication.latestForDiscovery | 70dfe028-027a-4dec-b6e3-1a49c9be9e60 |