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US 6,903,043 B2Granted
Chiral polymeric salen catalyst, and a process for preparing chiral compounds from racemic epoxides by using them
AssigneeRstech Co., Ltd.
InventorsGeon-Joong Kim, Dae-Woon Park, Ho Seong Lee, Seong Jin Kim
Life of this patent
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Abstract
The present invention relates to chiral salen catalysts and a process for preparing chiral compounds from racemic epoxides by using them. More particularly, the present invention is to provide a chiral polymeric salen catalyst and its use for producing chiral compounds such as chiral epoxides and chiral 1,2-diols economically in high yield and high optical purity by performing stereoselective hydrolysis or racemic epoxides.
Claims10
A chiral polymeric salen catalyst of formula (1),
- wherein
- R1, R2, R3, X1, X2, X3, X4, X5, X6, Y1, and Y2 represent individually a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxy, amino, thiol, nitro, amine, amide, carbonyl, carboxyl, silyl, ether, thioether, salenoether, ketone, aldehyde, ester, phosphoryl, phosphonate, phosphine, sulfonyl, or (CH2)k—R4,
- where R4 is phenyl, cycloalkyl, or cycloalkenyl,
- k is an integer of 0 to 8, and
- any two of R1, R2, or R3, can be bonded to each other to form a carbocycle containing 4 to 10 atoms;
- M represents a metal atom chosen from Co, Cr, V, Fe, Mo, W, and Ru;
- Z represents PF6, or BF4;
- m is an integer of 8 to 20;
- n is an integer of 1 to 6;
- and
- with the proviso that R3 is not a hydrogen atom, halogen, hydroxy, amino, nitro, amine or amide.
8 more elements
A method for preparing chiral polymeric salen catalyst of formula (1) comprising the following steps:
- reaction of phenol derivative of formula (2) with diamine derivative of formula (3) to produce polymeric salen ligand of formula (4);
- and
- introduction of a center metal (M) and counter ions (Z) to the obtained polymeric salen catalyst of formula (1),
- wherein
- R1, R2, R3, X1, X2, X3, X4, X5, X6, Y1, and Y2 represent individually a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxy, amino, thiol, nitro, amine, amide, carbonyl, carboxyl, silyl, ether, thioether, salenoether, ketone, aldehyde, ester, phosphoryl, phosphonate, phosphine, sulfonyl, or (CH2)k—R4,
- where R4 is phenyl, cycloalkyl, or cycloalkenyl,
- k is an integer of 0 to 8, and
- any two of R1, R2, or R3, can be bonded to each other to form a carbocycle containing 4 to 10 atoms;
- M represents a metal atom chosen from Co, Cr, V, Fe, Mo, W, and Ru;
- Z represents PF6, or BF4;
- m is an integer of 8 to 20;
- n is an integer of 1 to 6;
- and
- with the proviso that R3 is not a hydrogen atom, halogen, hydroxy, amino, nitro, amine or amide.
11 more elements
Dependencies are inferred from the claim text.