Unusual amino acids. I: Asymmetric synthesis of furylalanine derivatives.
Nonproteinogenic amino acids are valuable active compounds from their pharmacological and biochemical effects and also as novel building blocks for peptides. The preparation of furylalanine derivatives by asymmetric hydrogenation is described. Amino-phosphine-phosphinite-rhodium complexes catalyzed the hydrogenation of the prochiral dehydroamino acid precursors in high rate and with enantioselectivities of 70-90% ee. Substrate-catalyst ratios up to 2,000 can be used depending on the catalyst applied. The procedure turns out to be suitable for larger scale preparations.
Krause
H W
HW
Central Institute of Organic Chemistry, Division of Complex Catalysis, Rostock, Germany.
Wilcke
F W
FW
Kreuzfeld
H J
HJ
Döbler
C
C
D000596:Amino Acids / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D006865:Hydrogenation; D009942:Organometallic Compounds / Q000138:chemical synthesis; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D005663:Furans; D009942:Organometallic Compounds; D012238:Rhodium