Kinetic resolution of allylic esters in palladium-catalyzed asymmetric allylic alkylations using C–N bond axially chiral aminophosphine ligands

Chiral allylic esters, such as (R)-1,3-diphenyl-2-propenyl acetate (R)-2a, were synthesized by kinetic resolution in a palladium-catalyzed asymmetric allylic alkylation using N-aryl indoline type C–N bond axially chiral aminophosphines (S)-1 as ligands.

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(R)-1,3-Diphenylprop-2-en-1-yl acetateC17H16O2Ee = 95% (chiral HPLC)[α]D20=-4.9 (c 0.30, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-1,3-Diphenylprop-2-en-1-yl pivalateC20H22O2Ee = 55% (chiral HPLC)[α]D20=+3.4 (c 0.35, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-1,3-Diphenylprop-2-en-1-yl benzoateC22H18O2Ee = 59% (chiral HPLC)[α]D20=+8.0 (c 0.30, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)