Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
DIASTEREOSELECTIVE ALKYLATION OF 8-PHENYLMENTHYL PHENYLACETATE - AGGREGATED LITHIUM ENOLATE VERSUS NAKED ENOLATE
Autore:
SOLLADIECAVALLO A; CSAKY AG; GANTZ I; SUFFERT J;
Indirizzi:
EHICS,STEREOCHIM ORGANOMET LAB,1 RUE B PASCAL F-67008 STRASBOURG FRANCE
Titolo Testata:
Journal of organic chemistry
fascicolo: 18, volume: 59, anno: 1994,
pagine: 5343 - 5346
SICI:
0022-3263(1994)59:18<5343:DAO8P->2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
2-ARYLPROPIONIC ACIDS; ASYMMETRIC-SYNTHESIS; ESTERS; BASES; REARRANGEMENT; METHYL;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
25
Recensione:
Indirizzi per estratti:
Citazione:
A. Solladiecavallo et al., "DIASTEREOSELECTIVE ALKYLATION OF 8-PHENYLMENTHYL PHENYLACETATE - AGGREGATED LITHIUM ENOLATE VERSUS NAKED ENOLATE", Journal of organic chemistry, 59(18), 1994, pp. 5343-5346

Abstract

It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to69/31) and high yields (75 to 98%) while alkylation using tBu-P4 (a strong and cation free base, known to provide ''naked'' anion) leads tohigh diastereoselectivities (92/8 to 98/2) and high yields (65 to 95%). It is postulated that, in the case of phenylacetates, the degree ofaggregation of the lithium enolate is responsible of the poor diastereoselectivities.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 23:42:15