Diastereoselective Protocols for the Synthesis of 2,3-trans- and 2,3-cis-6-Methoxy-morpholine-2-carboxylic Acid Derivatives (Articolo in rivista)

Type

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

Label

• Diastereoselective Protocols for the Synthesis of 2,3-trans- and 2,3-cis-6-Methoxy-morpholine-2-carboxylic Acid Derivatives (Articolo in rivista) (literal)

Anno

• 2012-01-01T00:00:00+01:00 (literal)

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

• 10.1021/jo300221y (literal)

Alternative label

• Penso, Michele; Foschi, Francesca; Pellegrino, Sara; Testa, Andrea; Gelmi, Maria Luisa (2012)
  Diastereoselective Protocols for the Synthesis of 2,3-trans- and 2,3-cis-6-Methoxy-morpholine-2-carboxylic Acid Derivatives
  in Journal of organic chemistry
  (literal)

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

• Penso, Michele; Foschi, Francesca; Pellegrino, Sara; Testa, Andrea; Gelmi, Maria Luisa (literal)

Pagina inizio

• 3454 (literal)

Pagina fine

• 3461 (literal)

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

• http://pubs.acs.org/journal/orlef7 (literal)

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

• 77 (literal)

Rivista

• Journal of organic chemistry (Rivista)

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

• 8 (literal)

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

• 7 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• Consiglio Nazionale delle Ricerche (CNR); University of Milan (literal)

Titolo

• Diastereoselective Protocols for the Synthesis of 2,3-trans- and 2,3-cis-6-Methoxy-morpholine-2-carboxylic Acid Derivatives (literal)

Abstract

• Two diastereoselective and straightforward protocols for the high-yielding synthesis of 2,3-trans- and 2,3-cis-6-methoxy-3-substituted morpholine-2-carboxylic esters were realized in few steps, through the condensation between 5,6-diethoxy-5,6-dimethyl-1,4-dioxan-2-one and an appropriate imine, which is the key reaction to control the C2-C3 relative stereochemistry, followed by a methanolysis/ring-closure tandem reaction sequence. In particular, 2,3-trans-morpholines derive from the R*,S*-product of the acid condensation of N-functionalized alkylimines with the silylketene acetal of the above lactone, whereas 2,3-cis-morpholines derive from the R*,R*-product of basic condensation of an N-tosylimines with the lactone. (literal)

Prodotto di

• Institute of molecular science and technologies (ISTM) (Istituto)

Autore CNR

• MICHELE PENSO (Persona)

Incoming links:

Prodotto

• Institute of molecular science and technologies (ISTM) (Istituto)

Autore CNR di

• MICHELE PENSO (Persona)

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

• Journal of organic chemistry (Rivista)