Deoxycholic acid derived monophosphites as chiral ligands in the asymmetric Suzuki–Miyaura cross-coupling

Biaryl phosphites derived from deoxycholic acid were used as chiral ligands in the asymmetric Suzuki–Miyaura cross-coupling of arylboronic acids with aryl bromides. Amongst the different reaction parameters, the role of the base emerged as being crucial for the outcome of the reaction: the choice of base, and its amount, allowed enantiomerically enriched biaryl derivatives to be obtained at 1% catalyst loading and with an L:Pd ratio of 1:1.

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(+)-2-Methoxy-1-(2-formylphenyl)-naphthaleneC18H14O2[α]D28=+33.6 (c 0.5, CH2Cl2) for 27% eeSource of chirality: asymmetric synthesis

(+)-2-Methoxy-1-(2-methoxyphenyl)-naphthaleneC18H16O2[α]D28=+12.7 (c 0.41, CH2Cl2) for 24% eeSource of chirality: asymmetric synthesis

(+)-2-Methoxy-1-(2-methylphenyl)-naphthaleneC18H16O[α]D28=+19.4 (c 1, CH2Cl2) for 46% eeSource of chirality: asymmetric synthesis