Patent ID: 7541456

Claim:
A method for synthesizing a sugar molecule, comprising contacting at least one enolizable aldehyde α-substituted with a protected hydroxyl group with a catalytically effective amount of a nonmetallic chiral catalyst under conditions effective to allow the at least one enolizable aldehyde to undergo an enantioselective aldol coupling reaction, wherein the chiral catalyst is a secondary amine that has the structure of formula (VIIA) or (VIIB) wherein: R 8 is selected from hydrogen, hydroxyl, sulfhydryl, carboxyl, amino, mono-(C 1 -C 24 alkyl)-substituted amino, di-(C 1 -C 24 alkyl)-substituted amino, mono-(C 5 -C 24 aryl)-substituted amino, di-(C 5 -C 24 aryl)-substituted amino, di-N-(C 1 -C 24 alkyl)-N-(C 5 -C 24 aryl)-substituted amino, C 2 -C 24 alkylamido, C 6 -C 24 arylamido, imino, C 2 -C 24 alkylimino, C 6 -C 24 arylimino, nitro, nitroso, C 1 -C 24 alkoxy, C 5 -C 24 aryloxy, C 6 -C 24 aralkyloxy, C 2 -C 24 alkylcarbonyl, C 6 -C 24 arylcarbonyl, C 2 -C 24 alkylcarbonyloxy, C 6 -C 24 arylcarbonyloxy, C 2 -C 20 alkoxycarbonyl, C 6 -C 24 aryloxycarbonyl, halocarbonyl, carbamoyl, mono-(C 1 -C 24 alkyl)-substituted carbamoyl, di-(C 1 -C 24 alkyl)-substituted carbamoyl, di-N—(C 1 -C 24 alkyl)-N—(C 5 -C 24 aryl)-substituted carbamoyl, mono-(C 5 -C 24 aryl)-substituted carbamoyl, di-(C 5 -C 24 aryl)-substituted carbamoyl, thiocarbamoyl, mono-(C 1 -C 24 alkyl)-substituted thiocarbamoyl, di-(C 1 -C 24 alkyl)-substituted thiocarbamoyl, di-N—(C 1 -C 24 alkyl)-N—(C 5 -C 24 aryl)-substituted thiocarbamoyl, mono-(C 5 -C 24 aryl)-substituted thiocarbamoyl, di-(C 5 -C 24 aryl)-substituted thiocarbamoyl, carbamido, formyl, thioformyl, sulfo, sulfonato, C 1 -C 24 alkylthio, C 5 -C 24 arylthio, C 1 -C 24 alkyl, substituted C 1 -C 24 alkyl, C 1 -C 24 heteroalkyl, substituted C 1 -C 24 heteroalkyl, C 5 -C 24 aryl, substituted C 5 -C 24 aryl, C 1 -C 24 heteroaryl, substituted C 1 -C 24 heteroaryl, C 2 -C 24 aralkyl, substituted C 6 -C 24 aralkyl, C 2 -C 24 heteroaralkyl, and substituted C 2 -C 24 heteroaralkyl; R 13 is selected from C 1 -C 12 hydrocarbyl, substituted C 1 -C 12 hydrocarbyl, heteroatom-containing C 1 -C 12 hydrocarbyl, and substituted heteroatom-containing C 1 -C 12 hydrocarbyl; R 16 and R 17 are independently selected from hydrogen, halo, hydroxy, C 1 -C 12 hydrocarbyl, substituted C 1 -C 12 hydrocarbyl, heteroatom-containing C 1 -C 12 hydrocarbyl, and substituted heteroatom-containing C 1 -C 12 hydrocarbyl; and R 18 is a cyclic group optionally substituted with 1 to 4 non-hydrogen substituents and containing zero to 3 heteroatoms, or an acid addition salt thereof.