| dc.creator | Maldaner, AO | |
| dc.creator | Pilli, RA | |
| dc.date | 1999 | |
| dc.date | 43770 | |
| dc.date | 2014-12-02T16:25:12Z | |
| dc.date | 2015-11-26T16:12:58Z | |
| dc.date | 2014-12-02T16:25:12Z | |
| dc.date | 2015-11-26T16:12:58Z | |
| dc.date.accessioned | 2018-03-28T23:00:56Z | |
| dc.date.available | 2018-03-28T23:00:56Z | |
| dc.identifier | Tetrahedron. Pergamon-elsevier Science Ltd, v. 55, n. 47, n. 13321, n. 13332, 1999. | |
| dc.identifier | 0040-4020 | |
| dc.identifier | WOS:000083407900001 | |
| dc.identifier | 10.1016/S0040-4020(99)00835-2 | |
| dc.identifier | http://www.repositorio.unicamp.br/jspui/handle/REPOSIP/75211 | |
| dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/75211 | |
| dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/75211 | |
| dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1267333 | |
| dc.description | Alkylation of enolates of monosubstituted N-Boc lactams 4-6 afforded trans-disubstituted lactams as the major isomer. In the pyrrolidinone series, 1,3-induction seems to be ruled by steric interactions and the diastereoselection is low for the alkylation of enolates with small substituents at C-5 (e.g., Me) and methyl iodide. The trans selectivity improves with bulkier substituents at C-2 and/or bulkier electrophiles. The formation of 3,6-trans-disubstituted piperidinones benefits from the axial orientation of the substituent at C-2 due to the A(1,3) strain with the N-Boc group and excellent trans preference is observed even in the alkylation of the lithium enolate of N-Boc-6-methyl piperidinone with methyl iodide. (C) 1999 Elsevier Science ltd. All rights reserved. | |
| dc.description | 55 | |
| dc.description | 47 | |
| dc.description | 13321 | |
| dc.description | 13332 | |
| dc.language | en | |
| dc.publisher | Pergamon-elsevier Science Ltd | |
| dc.publisher | Oxford | |
| dc.publisher | Inglaterra | |
| dc.relation | Tetrahedron | |
| dc.relation | Tetrahedron | |
| dc.rights | fechado | |
| dc.rights | http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy | |
| dc.source | Web of Science | |
| dc.subject | disubstituted pyrrolidinones and piperidinones | |
| dc.subject | alkylation | |
| dc.subject | steric and stereoelectronic effects | |
| dc.subject | Acid | |
| dc.subject | Stereochemistry | |
| dc.title | Stereoselective alkylation of N-Boc-2-pyrrolidinones and N-Boc-2-piperidinones. Synthesis and characterization of disubstituted lactams | |
| dc.type | Artículos de revistas | |
