A chiral diaryl prolinol silyl ether organocatalyst with an acid is used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in good yields and with excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.
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Hayashi et al. (2008) studied this question.
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