The enantioselective synthesis of L- and D-carboranylalanine is reported. Imides 13 and 14 are treated with titanium tetrachloride, DIEA, and NBS to introduce a bromo functionality in 98:2 ratio at the alpha-center. Azide displacement with TMGA, displacement of the oxazolidinone template with titanium tetrabenzyloxide, and subsequent hydrogenolysis permits L- or D-carboranylalanine to be isolated in high stereoselectivity and 35-40% yields overall.
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Radel et al. (1996) studied this question.
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