The lithium enolate generated from t-butyl (bornylideneamino)acetate and butyllithium in the presence of t-butyl alcohol undergoes highly diastereoselective asymmetric Michael addition with a variety of α,β-unsaturated esters to afford the anti derivatives of 3-substituted glutamates with 2R-configuration as major products. Use of 2-alkylidenemalonates as Michael acceptors leads to 100% diastereoselective Michael additions.
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Kanemasa et al. (1989) studied this question.
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