Preparation and reactions of stannylated amino acids.
Hydrostannations of propargylic glycine esters with the new hydrostannation catalyst [Mo(CO)3(CNtBu)3] (MoBI3) gave rise to alpha-stannylated allylic esters in good yield and with high regioselectivity. The chelate Claisen rearrangements of these esters allow the syntheses of gamma,delta-unsaturated amino acids with a vinylstannane moiety in the side chain. The amino acids obtained can be further modified by cross-coupling with various types of electrophiles.
Kazmaier
U
U
Organisch-Chemisches Institut der Universität Heidelberg, Germany.
Schauss
D
D
Raddatz
S
S
Pohlman
M
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014001:Tin / Q000737:chemistry*
D000596:Amino Acids; D014001:Tin