Enantioselective ring opening of epoxides with TMSN3 by macrocyclic oligomer-supported Cr(III)–salen catalysts

Three Cr(III)–salen catalysts supported onto macrocyclic oligomeric cyclooctene through linkers of different lengths were synthesized. The influences of the linker length and the oligomeric support on the activity and the enantioselectivity of catalysts were investigated in the asymmetric ring opening of a meso-epoxide and the kinetic resolution of terminal epoxides. For both reactions all three catalysts exhibited significantly higher catalytic efficiency than the unsupported monomeric Cr(III)–salen catalyst. The catalyst with the shortest linker 1 showed the highest reaction rate while the catalyst with the longest linker 3 afforded the highest enantioselectivity in both reactions. The recoverability of catalyst 1 was also studied.

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