Enantioselective synthesis of anti-beta-substituted gamma,delta-unsaturated amino acids: a highly selective asymmetric thio-Claisen rearrangement.
A novel synthesis of optically active anti-beta-substituted gamma,delta-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.
Liu
Zhihua
Z
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Qu
Hongchang
H
Gu
Xuyuan
X
Min
Byoung J
BJ
Nichol
Gary S
GS
Nyberg
Joel
J
Hruby
Victor J
VJ
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013455:Sulfur / Q000737:chemistry*
D000596:Amino Acids; D013455:Sulfur