Jacobsen Assymetric Epoxidation Reaction

Jacobsen Assymetric Epoxidation Reaction - Myers Reviews:...

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R' R O CH 3 CH 3 NC O O O CH 3 CH 3 O NC O O O O R' R O H H t -Bu t -Bu NN t -Bu t -Bu O O Mn Cl H H Ph CH 3 Ph H R' H R t -Bu t -Bu t -Bu t -Bu O O Mn H H O R' H R H Ph Ph Ph H 3 C Ph Ph Ph Ph O H 3 C Ph Ph O Ph Ph Ph O R R" H R' Ph CH 3 Ph O H Chem 2 15 Jacobsen Asymmetric Epoxidation Reaction Myers Reviews: Jacobsen, E. N. In Catalytic Asymmetric Synthesis , Ojima, I., Ed.; VCH: New York, 1993 ; pp. 159-202. Linker, T. Angew. Chem. , Int. Ed. Engl. 1997 , 36 , 2060-2062. ( S , S )- 1 ( S , S )- 1 (4 mol %) NaOCl(aq) CH 2 Cl 2, 4 °C olefin yield, % ee, % equiv ( S , S )- 1 96 63 97 94 0.03 0.15 79 84 0.006 a Selectivity is determined through nonbonded interactions. Terminal olefins are poor substrates. Addition of substoichiometric amounts of 4-phenylpyridine N -oxide improves both catalyst a Reaction carried out in the presence of 4-phenylpyridine N -oxide. The observed selectivities have been explained cis -Disubstituted conjugated olefins are epoxidized with high levels of enantioselectivity.
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This note was uploaded on 04/07/2008 for the course CHEM 215 taught by Professor Shair during the Fall '07 term at Harvard.

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Jacobsen Assymetric Epoxidation Reaction - Myers Reviews:...

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