Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex
AssigneeCalifornia Institute of Technology
InventorsJohn HARTUNG, Robert H. GRUBBS
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Abstract
This invention relates generally to enantiomerically enriched C—H activated ruthenium olefin metathesis catalyst compounds which are stereogenic at ruthenium, to the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in enantio- and Z-selective olefin metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.
Claims13
An enantioenriched C—H activated catalyst compound having the structure of formula (II):
- wherein,
- M is a Group 8 transition metal;
- L1 is a neutral electron donor ligand;
- Q* is a two electron anionic donor bridging moiety linking R3 and M;
- Q is a linker selected from hydrocarbylene, substituted hydrocarbylene, heteroatom-containing hydrocarbylene, and substituted heteroatom-containing hydrocarbylene linkers;
- X is an atom selected from C, N, O, S, and P;
- R1 and R2 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing, hydrocarbyl, and functional groups;
- R3 and R4 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing, hydrocarbyl, and functional groups;
- n is zero, 1, or 2, such that n is zero when X is O or S, n is 1 when X is N or P, and n is 2 when X is C;
- and
- X1 is a bidentate anionic ligand.
An enantioenriched C—H activated catalyst compound, selected from
A method, comprising:
- contacting an α-olefin with a strained olefin, in the presence of an enantioenriched C—H activated catalyst under conditions and for a time period effective to allow an asymmetric ring opening cross metathesis reaction to occur.
A method, comprising:
- reacting an α-olefin with a strained olefin, in the presence of an enantioenriched C—H activated catalyst, to form an asymmetric ring opening cross metathesis product with a Z:E ratio greater than 1:1 in favor of the Z-isomer.
Dependencies are inferred from the claim text.