By Ojima I.
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Extra info for Applications II. Transition Metal Compounds in Organic Synthesis 1
As shown in Scheme 5, 99% ee was obtained in the hydrogenation of both 2-acetylamino-cyclopent-1-enecarboxylic acid methyl ester and ethyl ester. A heterocyclic 3-(acylamino)acrylate is also hydrogenated to give cis-product with excellent enantioselectivity (95% ee). 28 The N-acyl protecting group is considered indispensable to satisfy the chelation requirment with transtion metal, leading to high reactivity and enantioselectivity for the hydrogenation of unsaturated -amino acid. Recently, Haiso et al.
C S/C ratio ¼ 10,000. b derivatives, achieving high enantioselectivities for the (Z)-isomeric substrates is more important for the practical synthesis of chiral 3-aryl-3-amino acids via the asymmetric hydrogenation. Few efficient ligands have been reported for the hydrogenation of (Z)-3-aryl-3-(acylamino)acrylates. Xylyl–BINAPO–Ru catalyst,140 TangPhos–Rh catalyst,115 BINAPINE–Rh,113 and hybrid ferrocenylphosphine–phosphoramidite 75156a are found to be effective for the reactions of a variety of (Z)-3-aryl-3-(acylamino)acrylates.
It is believed that the amino group of the ligand interacts with the carboxylic acid functionality of the substrate, hence facilitating the olefin coordination to the Rh center. When substrates with two different substituents at the -positions are employed, the hydrogenation products with two chiral centers can be efficiently obtained. (ii) ,-Unsaturated esters, amides, lactones, and ketones Limited progress has been achieved in the asymmetric hydrogenation of ,-unsaturated carboxylic acid esters, amides, lactones, and ketones.
Applications II. Transition Metal Compounds in Organic Synthesis 1 by Ojima I.