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Asymmetric 1,4 addition of Grignard reagents to chiral alpha,beta-unsaturated esters in the presence of Lewis acids



Asymmetric 1,4 addition of Grignard reagents to chiral alpha,beta-unsaturated esters in the presence of Lewis acids



Tetrahedron 55(19): 6231-6242



The synthesis of enantiomerically enriched alpha-amino acids is described, by means of the diastereoselective conjugate addition of Grignard reagent to (S)-2-acetamidoacrylic ethoxycarbonyl-phenyl-methyl ester 1 and its N-Boc derivative 5 in the presence of Lewis acids. The addition of magnesium organocuprates has also been analysed. The reaction proceeds with good yields and variable diastereoselectivities, depending on the organometallic reagent and on the Lewis acid utilised.

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