Stereoselective ring opening reactions
AssigneePresident and Fellows of Harvard College
InventorsEric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
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Abstract
The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
Claims29
A kinetic resolution process, comprising the step of reacting water and a mixture of stereoisomers of a chiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce by kinetic resolution a stereoisomerically enriched cyclic substrate or a stereoisomerically enriched hydrolysis product or both, wherein said cyclic substrate comprises a carbocycle or heterocycle having a reactive center susceptible to nucleophilic attack by said water, and said chiral catalyst comprises an asymmetric tetradentate ligand complexed with a metal atom, which complex has a rectangular planar or rectangular pyramidal geometry.
A kinetic resolution process, comprising the step of reacting water and a mixture of stereoisomers of a chiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce by kinetic resolution a stereoisomerically enriched cyclic substrate or a stereoisomerically enriched hydrolysis product or both, wherein said cyclic substrate comprises a carbocycle or heterocycle having a reactive center susceptible to nucleophilic attack by said water, and said chiral catalyst comprises an asymmetric tridentate ligand complexed with a metal atom, which complex has a trigonal planar or trigonal pyramidal geometry.
Dependencies are inferred from the claim text.