The preparation of cis-2,3-dihydrobenzofuranols
with two stereocenters through aqueous asymmetric transfer hydrogenation
(ATH) of benzofuranones with the metal catalyst Ru(II) via dynamic
kinetic resolution (DKR) has been developed. A variety of α-alkyl benzofuranones were transformed
to obtain optically pure 2,3-dihydrobenzofuran-3-ols with excellent
enantioselectivities and acceptable yields under mild conditions.
A handy and effective method was established to obtain the cis-2,3-dihydrobenzofuranols having three stereocenters, involving asymmetric transfer hydrogenation of benzofuranones via dynamic kinetic resolution. The general applicability of this method was examined with different benzofuran-3-(2 H)-ones, and stereoselectivities of 85-99% ee and up to 98/2 dr were obtained.
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