Journal of Organic Chemistry p. 9648 - 9660 (2019)
Update date:2022-08-25
Topics:
Prasad, Kavirayani R.
Uphade, Manoj B.
A regio- and diastereoselective conjugate addition of the lithium anion of N-allyl imine (prepared from allylamine and benzophenone) to α,β-unsaturated esters in good yields is reported. The reaction was general and provided the γ-amino esters resulting from the regioselective C-C bond formation between the α-carbon to the nitrogen in the imine and the β-carbon of the unsaturated ester. Synthetic utility of the formed products was illustrated in the nonracemic total synthesis of the bioactive alkaloid (-)-epibatidine.
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