2.4- Hexadien kinetic resolution

One especially interesting kinetic resolution/ asymmetric epoxidation substrate is (R,S)-2,4-hexadien-3-ol (80) [77]. The racemic diene has eight different olefinic faces at which epoxidation can occur and thereby presents an interesting challenge to the selectivity of the epoxidation catalyst. The selectivity can be tested by using slightly less than 0.5 equiv. of oxidant (because the substrate is a racemate, the maximum yield of any one product is 50%). When the reaction was run under these conditions, the only product that was formed was the (l/f,2/f,3/f)-epoxy alcohol 81. 

In addition, the kinetic resolution of (2,4-hexadien-l-al)-FE(CO)3 or of (2,4-hexad-ien-l,6-dial)-Fe(CO)3 with BY proceeded with high efficiency and enantioselectivity [222]. Recently, the course of the asymmetrical reduction of acyclic (diene)-FE(CO)3 complexes... 

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