Organocatalysts and Methods of Use in Chemical Synthesis

摘要

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo-selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH₂, N-R^a, O, S or C-O; Y is CH₂, N-R^a, O, S or C-O, with the proviso that at least one of X or Y is CH₂, and preferably both of X and Y are CH₂; R^a is H, an optionally substituted C₁-C₁₂ alkyl, preferably an optionally substituted C₁-C₆alkyl including a C₃-C₆ cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; R^b is H, an optionally substituted C₁-C₁₂ alkyl, preferably an optionally substituted C₁-C₆ acyclic or a a C₃-C₆ cyclic alkyl group, CIIO, N(Me)O, CO(S)R^a or the group of Formula (III). Where R^c and R^d are each independently H, F, Cl, an optionally substituted C₁-C₂₀ alkyl, preferably an optionally substituted C₁-C₁₂ alkyl, more preferably a C₁-C₆ alkyl, and an optionally substituted aryl group, or together R^c and R^d form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R¹ is OH, OR, NR'R'', NHC(-O)R, NHSO₂R; R² is H, F, Cl, an optionally substituted C₁-C₂₀ alkyl, preferably an optionally substituted C₁C₆ alkyl, an optionally substituted aryl group or a -O group (which establishes a carbonyl group with the carbon to which -O is attached; R³ is H, OH, F, Cl, Br, I, Cl, an optionally substituted C₁-C₂₀ alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C₁-C₆ alkyl, or an optionally substituted aryl, such that the carbon to which R³ is attached has an R or S configuration; R is II, an optionally substituted C₁-C₂₀ alkyl, preferably an optionally substituted C₁-C₆ alkyl, or an optionally substituted aryl group, R' and R'' are each independently H, an optionally substituted C₁-C₂₀ alkyl group, preferably an optionally substituted C₁-C₆ alkyl, or an optionally substituted aryl group; or together R' and R'' form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R'' are attached; and wherein said compound is free from a metal catalyst.