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Titolo:
ZIRCONOCENE-CATALYZED EPOXY ESTER ORTHO ESTER REARRANGEMENT - A NEW METHOD FOR THE PROTECTION OF POLYFUNCTIONALIZED CARBOXYLIC-ACIDS AND THE ASYMMETRIC-SYNTHESIS OF ORTHO ESTERS
Autore:
WIPF P; XU WJ; KIM H; TAKAHASHI H;
Indirizzi:
UNIV PITTSBURGH,DEPT CHEM PITTSBURGH PA 15260
Titolo Testata:
Tetrahedron
fascicolo: 48, volume: 53, anno: 1997,
pagine: 16575 - 16596
SICI:
0040-4020(1997)53:48<16575:ZEEOER>2.0.ZU;2-T
Fonte:
ISI
Lingua:
ENG
Soggetto:
L-VINYLGLYCINE; AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; STEREOSELECTIVE SYNTHESIS; CONVENIENT SYNTHESIS; L-HOMOSERINE; COMPLEXES; CHEMISTRY; BETA;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
44
Recensione:
Indirizzi per estratti:
Citazione:
P. Wipf et al., "ZIRCONOCENE-CATALYZED EPOXY ESTER ORTHO ESTER REARRANGEMENT - A NEW METHOD FOR THE PROTECTION OF POLYFUNCTIONALIZED CARBOXYLIC-ACIDS AND THE ASYMMETRIC-SYNTHESIS OF ORTHO ESTERS", Tetrahedron, 53(48), 1997, pp. 16575-16596

Abstract

In situ prepared Cp-2(Cl)Zr+ catalyzes the formation of ortho esters from epoxy esters. Acid-sensitive alpha-amino and alpha-hydroxy acid derivatives are converted in high yield to 2,7,8-trioxabicyclo[3.2.1]octanes (ABO-esters) using this protocol. This strategy is complementaryto the OBO-ester technology, and orthogonal methods for the deprotection of ABO- and OBO-esters have been developed. The syntheses of the mushroom components (S)-gamma-hydroxyleucine lactone and (S)-alpha-vinylglycine underline the value of ABO-ester protective group strategy. Using chiral epoxy alcohol derivatives, the first convenient and general asymmetric synthesis of bicyclic ortho esters has been achieved. (C)1997 Elsevier Science Ltd.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 12/08/20 alle ore 19:20:35