Enantioselective Hydrogenation of Tetrasubstituted Olefins of Cyclic β-(Acylamino)acrylates

• Published in: Journal of the American Chemical Society Vol. 125; no. 32; pp. 9570 - 9571
• Main Authors: Tang, Wenjun, Wu, Shulin, Zhang, Xumu
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.08.2003; Amer Chemical Soc
• Subjects: Acrylates - chemistry; Amino Acids, Cyclic - chemical synthesis; Chemical reactivity; Chemistry; Chemistry, Multidisciplinary; Cycloparaffins - chemistry; Exact sciences and technology; Hydrogenation; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; Stereoisomerism; RHODIUM-CATALYZED HYDROGENATION; AMINO ACID-DERIVATIVES; EFFICIENT ASYMMETRIC-SYNTHESIS; LIGANDS; BETA-PEPTIDES; CISPENTACIN; Catalytic reaction; Enantioselectivity; Catalyst selectivity; Transition metal Complexes; Complex catalyst; Experimental study; Hydrogenation; Asymmetric reaction; Ruthenium Complexes; Platinoid Complexes; Catalyst activity; Monocyclic compound; Ethylenic compound
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja035777h

Hydrogenation of a series of cyclic β-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic β-amino acid derivatives.