Practical, Highly Enantioselective Chemoenzymatic One-Pot Synthesis of Short-Chain Aliphatic beta-Amino Acid Esters

Weiss M, Gröger H. Practical, Highly Enantioselective Chemoenzymatic One-Pot Synthesis of Short-Chain Aliphatic beta-Amino Acid Esters. SYNLETT. 2009;2009(08):1251-1254.A practical, highly enantioselective method for the synthesis of short-chain aliphatic beta-amino acid esters was developed starting from prochiral and easily accessible Substrates. This chemoenzymatic approach is based oil a nonenzymatic aza-Michael addition of benzylamine to enoates and subsequent lipase-catalyzed resolution via enantioselective aminolysis. The two reactions are carried out as a one-pot synthesis under solvent free-conditions affording the beta-amino esters in satisfying to good yields and with excellent enantioselectivities of up to 99% ee