New chiral bis(phosphinoamides) based on glucose 1G and mannose 1M have been prepared. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopenten-2-ene-1,4-diol biscarbamate in high ee’s (up to 97%). Glucose and mannose moieties selectively promote formation of the opposite enantiomers, as a consequence of inverted steric motifs around the metal center.
Bis(phosphinoamides) based on sugars for highly enantioselective allylic substitution: inversion of stereocontrol by switching from glucose to mannose / Ruffo, Francesco; DEL LITTO, Raffaella; DE ROMA, Antonella; D'Errico, A; Magnolia, S.. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 17:15(2006), pp. 2265-2269. [10.1016/j.tetasy.2006.07.032]
Bis(phosphinoamides) based on sugars for highly enantioselective allylic substitution: inversion of stereocontrol by switching from glucose to mannose
RUFFO, FRANCESCO;DEL LITTO, Raffaella;DE ROMA, ANTONELLA;
2006
Abstract
New chiral bis(phosphinoamides) based on glucose 1G and mannose 1M have been prepared. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopenten-2-ene-1,4-diol biscarbamate in high ee’s (up to 97%). Glucose and mannose moieties selectively promote formation of the opposite enantiomers, as a consequence of inverted steric motifs around the metal center.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
