A transition state of type 1 is involved in the enantioselective addition of diethylzinc to N-(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2-azanorbornyl-3-methanols. This was shown by quantum chemical calculations, which were also used to identify the factors responsible for the selectivity. An efficient route to both diastereomers of new bicyclic 2-azanorbornyl-3-methanols with an additional chiral center was developed, and in the best case, up to 97 % ee was obtained with these ligands.
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Brandt et al. (1999) studied this question.