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The diastereomeric ratios were determined by analogy
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The diastereomeric ratios were determined by analogy.
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78650172510
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note
-
The first C-C bond formation would be almost anti selective as depicted in Fig. 3 (see also Ref. 19) at low temperature. However, the enantioselectivity of this step would be low. If the enantio-determining step had been mainly this step, the enantiomeric excess of product 3a obtained under the conditions of entry 3 (Table 4) would have been at least 24% according to the results shown in entries 1 and 2. This assumption is evidently inconsistent with the actual result (9% ee). Therefore, the kinetic resolution of the anti iminium ion via the second intramolecular reduction would be mainly enantio-determining.
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