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;
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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/109812
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