Asymmetric Eschenmoser-Claisen rearrangement for anti-beta-substituted gamma,delta-unsaturated amino acids.
Optically active anti-beta-substituted gamma,delta-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.
Qu
Hongchang
H
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Gu
Xuyuan
X
Liu
Zhihua
Z
Min
Byoung J
BJ
Hruby
Victor J
VJ
D000596:Amino Acids / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000596:Amino Acids; D007211:Indoles; D007769:Lactams; D015032:Zinc