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Rück-Braun, K.; Freysoldt, T., Science of Synthesis, (2007) 35, 513.
The exchange of simple alkyl- or amino substituents at the boron atom by chiral substituents allows an enantioselective cleavage of meso-epoxides. The only known example for this application is the use of bromo(diisopinocampheyl)borane (42), of which both enantiomers are easily available from α-pinene. The reaction gives moderate to good yields and moderate enantioselectivities of bromo alcohols 43 from epoxides 41 (Scheme 17).[49] The optically pure compounds are obtained in up to 99% ee by simple recrystallization from pentane. The labile nature of the resulting bromo alcohols requires a nonoxidative workup procedure.
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References
| [49] | Meeee, M. M.; Meeeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
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