Synthesis of Enantiomerically Pure D??and L??(Heteroaryl) alanines by asymmetric hydrogenation of (Z)?螃窿?amino?螃力漫?didehydro esters

T Masquelin, E Broger, K Müller, R Schmid…

Index: Masquelin; Broger; Muller; Schmid; Obrecht Helvetica Chimica Acta, 1994 ,  vol. 77,  # 5  p. 1395 - 1411

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Citation Number: 48

Abstract

Abstract Homogeneous asymmetric hydrogenation of a wide range of methyl and tert-butyl (Z)-2-(acylamino)-3-(heteroaryl) acrylates (see 1a–f and 2a–d, f, g, resp.) catalyzed by diphosphinerhodium catalysts was studied for the synthesis of enantiomerically pure 3-furyl-, 3-thienyl-, and 3-pyrrolylalanines (see 3a–f, and 4a–d, g; Scheme 1). The precursors, the (Z)- α-amino-α, β-didehydro esters 1a–f and 2a–d, f, g were prepared in high yields using the ...