Synthesis and Applications of 3-[6-(Hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols or 3,3′-Bis[6-(hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols

Abstract

A series of new 1,1′-bi-2-naphthol (BINOL) derived ligands, 3-[6-(hydroxymethyl)pyridin-2-yl]-BINOLs or 3,3′-bis[6-(hydroxymethyl)pyridin-2-yl]-BINOLs, bearing one or two chiral pyridinylmethanols attached to a binaphthyl skeleton, have been synthesized using the Suzuki cross-coupling reaction. The resulting compounds have been used as ligands in the enantioselective addition of diethylzinc to aldehydes; the products were obtained with up to 96% ee.

Key word

pyridin-2-ylmethanol - BINOL - Suzuki cross-coupling reaction - asymmetric catalysis

References

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7

The product with one MOM removed was determined by ¹H NMR.