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Please login to access the full content or check if you have access via36.1.8.27 Method 27: Resolution of (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol
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Eames, J., Science of Synthesis, (2008) 36, 380.
The resolution of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (rac-103) using Pseudomonas AK and butanoic anhydride as the acyl donor in diisopropyl ether, has been probed (Scheme 57).[154] This process is moderately enantioselective, favoring the formation of the ester (R)-104 in 63% yield with 59% ee (derived from the S-alcohol) and recovered alcohol (R)-103 in 38% yield with >99% ee (E = 24–29 at 62% conversion). The enantiopurity of the ester (R)-104 can be increased by, firstly, sodium hydroxide mediated hydrolysis to give alcohol (S)-103 in 87% yield [64% ee; the starting ester (R)-104 is obtained by combining products from previous preparative scale resolutions], followed by a second resolution to give (R)-104 in 67% yield with 94% ee (at 71% conversion).[154,155] Simple hydrolysis of (R)-104 gives the complementary enantiomer (S)-103 in 63% yield with 94% ee.[154]
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References
| [154] | Mäeeeeeee, M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [155] | Mäeeeeeee, M.; Meeeeee, M. M., Meeeeeeeeee: Meeeeeeee, (8888) 8, 888. |
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