Oxime ethers Lewis acid coordination

In this model the sense of asymmetric induction is controlled by two principle factors (i) coordination of borane on the least-hindered face of the bicyclic ring system and (ii) coordination of the Lewis acid syn to the small group (R ). The latter point is in good agreement with the structural data that has been presented in this chapter, and is further supported by results from the asymmetric reduction of oxime ethers (Figure 51). As predicted by the model (75 and 78), (E) and (Z)-oxime ethers afford enantiomeric amines upon reduction by the reagent derived from (-)-norephedrine and borane (2 equiv.). Here, Lewis acid coordination is dictated by the ( )/(Z) stereochemistry of the oxime ether rather than by the rule of coordination syn to the small group. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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