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US 6,610,889 B2Granted
Catalytic compositions and methods for asymmetric aldol reactions
AssigneeThe Board of Trustees of the Leland Stanford Junior University
InventorsBarry M. Trost, Hisanaka Ito
Life of this patent
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Abstract
Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.
Claims11
A method of conducting an enantioselective aldol reaction between an aldehyde and a donor molecule selected from a ketone bearing an α-hydrogen and a nitroalkyl compound, the method comprising
- contacting said aldehyde and said donor molecule in the presence of a catalytic amount of an asymmetric catalyst, wherein said catalyst is a complex of a Group 2A or Group 2B metal with a chiral ligand of formula I:
- where
- R1-R4 are aryl groups, which may be the same or different, each of which is unsubstituted or substituted with one or more substituents X, where each X is independently selected from alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, aralkynyl, alkoxy, aryloxy, amide, alkyl- or aryl sulfonyl, sulfonamide, hydroxy, cyano, nitro, and halogen,
- wherein R1 and R2, or R3 and R4, or both of these combinations, may be linked at an α-carbon of each said group to form a tricyclic or larger ring system;
- m is an integer from 0 to 3;
- each of R5 and R6 represents one or more substituents independently selected from the group consisting of hydrogen and X as defined above;
- and
- R7 represents one or more substituents on the phenol ring independently selected from the group consisting of hydrogen, X as defined above, and a further fused ring;
- under conditions effective to produce an aldol reaction product which is enriched in one of the possible stereoisomeric products of such reaction.
6 more elements
Dependencies are inferred from the claim text.