syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives (Articolo in rivista) (literal)

Anno

• 2014-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1002/ejoc.201400142 (literal)

Alternative label

• Bonetti, Andrea; Clerici, Francesca; Foschi, Francesca; Nava, Donatella; Pellegrino, Sara; Penso, Michele; Soave, Raffaella; Gelmi, Maria Luisa (2014)
  syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives
  in European journal of organic chemistry (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Bonetti, Andrea; Clerici, Francesca; Foschi, Francesca; Nava, Donatella; Pellegrino, Sara; Penso, Michele; Soave, Raffaella; Gelmi, Maria Luisa (literal)

Pagina inizio

• 3203 (literal)

Pagina fine

• 3209 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

• http://onlinelibrary.wiley.com/journal/10.1002/%28ISSN%291099-0690 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 2014 (literal)

Rivista

• European journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 7 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 15 (literal)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• DISFARM, Universita degli Studi MilanoMilan, Italy; DISFARM;CNR-ISTM; DISFARM;DISFARM ; CNR-ISTM;CNR-ISTM; DISFARM (literal)

Titolo

• syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives (literal)

Abstract

• A very efficient synthesis of 2,3-diaryl-?-amino acid derivs. is realized by a TiCl4/Et3N-catalyzed Mannich-like reaction of arylacetic or arylthioacetic esters with aryl imines. The presence of an ortho-heteroatom group on the arylacetic moiety, able to coordinate to the Ti center, is of dramatic importance for the outcome of the reaction and to tune the syn/anti diastereoselection. In particular, with ortho-fluoro-, -chloro-, and -bromoarylacetates, the syn adduct was isolated as the largely prevalent isomer. When (-)-8-phenylmenthyl (2-fluorophenyl)acetate was used, the condensation with imines resulted in high diastereo- and enantioselectivity. In agreement with the stereochem. results and NMR, a conceivable reaction mechanism was proposed. (literal)

Prodotto di

• Istituto di scienze e tecnologie molecolari (ISTM) (Istituto)

Autore CNR

• RAFFAELLA SOAVE (Persona)
• MICHELE PENSO (Persona)

Insieme di parole chiave

• Keywords of "syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di scienze e tecnologie molecolari (ISTM) (Istituto)

Autore CNR di

• MICHELE PENSO (Persona)
• RAFFAELLA SOAVE (Persona)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• European journal of organic chemistry (Rivista)

Insieme di parole chiave di

• Keywords of "syn/anti Switching by specific heteroatom-titanium coordination in the Mannich-like synthesis of 2,3-diaryl-?-amino acid derivatives" (Insieme di parole chiave)