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35.2.5.2.8.1 Variation 1: Enantioselective Transformations

DOI: 10.1055/sos-SD-035-00442

Rück-Braun, K.; Freysoldt, T.Science of Synthesis, (200735513.

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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