Chirality control in the enantioselective arylation of aromatic aldehydes catalyzed by cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acid derived 1,3-aminoalcohols

A series of chiral 1,3-aminoalcohols derived from cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acid were synthesized and applied to the enantioselective arylation of aromatic aldehydes. The reactions exhibited good yields (up to 90%) and moderate to high enantioselectivities (up to 99%). Not only the enantioselectivity but also the stereochemistry of the product were controlled by the substituent effect of the chiral ligands.

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(1R,2S)-2-Piperidin-1′-ylcyclohexylmethanolC12H23NO[α]D26=+16.5 (c 0.4, CHCl3)Source of chirality: cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acidAbsolute configuration: (1R,2S)

(1R,2S)-(2-Benzylaminocyclohexyl)bis(3,5-dimethoxyphenyl)methanolC30H37NO5[α]D26=+64.7 (c 4.0, CHCl3)Source of chirality: cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acidAbsolute configuration: (1R,2S)