This process, as shown by curly arrows in 9.60, is facilitated by an interaction between the carbonyl oxygen atom and La 3. ![]() The activated CH 2NO 2 moiety thus produced attacks the C atom of the carbonyl group. Conversion of 9.12 to 9.59 is facilitated by the Brønsted base behavior of the Li–O bond and the Lewis acidity of La 3. In 9.59 one of the oxygen atoms of the nitro group coordinates to the La 3 cation. The Li–O bond marked by an arrow in 9.12 is cleaved due to protonation of the binaphthol oxygen atom by nitromethane. ![]() The proposed catalytic cycle for the nitroaldol condensation reaction is shown in Fig. ![]() The La–O bond marked by an arrow opens up due to protonation of the O atom by nitromethane. ![]() Figure 9.15 Catalytic cycle for asymmetric nitroaldol condensation reaction with 9.12 as the chiral catalyst.
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