Synthesis of Anti-beta-substituted gamma,delta-unsaturated amino acids via Eschenmoser-Claisen rearrangement.
Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.
Qu
Hongchang
H
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Gu
Xuyuan
X
Min
Byoung J
BJ
Liu
Zhihua
Z
Hruby
Victor J
VJ
D000596:Amino Acids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000596:Amino Acids