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Titolo:
BENZOTRIAZOLE-MEDIATED STEREOSELECTIVE OLEFINATION OF CARBOXYLIC ESTERS - TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS INTO CHIRAL ALLYLAMINES
Autore:
KATRITZKY AR; CHENG D; LI JQ;
Indirizzi:
UNIV FLORIDA,DEPT CHEM,CTR HETEROCYL CPDS GAINESVILLE FL 32611
Titolo Testata:
Journal of organic chemistry
fascicolo: 10, volume: 63, anno: 1998,
pagine: 3438 - 3444
SICI:
0022-3263(1998)63:10<3438:BSOOCE>2.0.ZU;2-Z
Fonte:
ISI
Lingua:
ENG
Soggetto:
LOW-VALENT TITANIUM; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALLYLIC AMINATION; DERIVATIVES; REAGENTS; ROUTE; 1,2-ADDITION; ALDEHYDES; KETONES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
44
Recensione:
Indirizzi per estratti:
Citazione:
A.R. Katritzky et al., "BENZOTRIAZOLE-MEDIATED STEREOSELECTIVE OLEFINATION OF CARBOXYLIC ESTERS - TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS INTO CHIRAL ALLYLAMINES", Journal of organic chemistry, 63(10), 1998, pp. 3438-3444

Abstract

Diastereoselective trans-olefinations of carboxylic esters 3a-h have been accomplished using benzylic or allylic benzotriazole derivatives la-e to prepare alpha-(benzotriazol-1-yl) ketones 4a-i, for the subsequent reduction of 4a-i, and finally for low-valent titanium-effected dehydroxybenzotriazolylation.(1) N-Protected alpha-amino acid esters 9a-c and 15 thus give allylamines 13a-e and 19 with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/06/20 alle ore 23:58:58