Diastereoselective Synthesis of d-Amino acids through Domino Ireland-Claisen Rearrangement and Michael Addition.

[摘要]：rearrangement and asym. Michael addn. - is described. A protocol starting from Baylis-Hillman adducts, e.g. R1CH:C(CH2OAc)CO2R2 (R1 = Ph, 3,4-(MeO)2C6H3, 3-pyridinyl, R2 = Me, tert-Bu), using a chiral lithium amide affords optically active g-substituted d-amino acids, e.g. I, with high diastereoselectivities and enantioselectivities. The acid can be isolated easily from large-scale reactions and transformed to 2,3-disubstituted piperidines II (R3 = CH2OH) or 2-substituted nipecotic acid derivs. II (R3 = CO2t-Bu).

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