Access to α,γ-Diamino Diacid Derivatives via Organocatalytic Asymmetric 1,4-Addition of Azlactones and Dehydroalanines

作者：Yang, Junxian; Sun, Wangsheng^*; He, Zeyuan; Yu, Changjun; Bao, Guangjun; Li, Yiping; Liu, Yuyang; Hong, Liang^*; Wang, Rui^*

来源：Organic Letters, 2018, 20(22): 7080-7084.

DOI：10.1021/acs.orglett.8b03020

• ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION
• SOLID-PHASE SYNTHESIS
• ALPHA-AMINO-ACIDS
• GAMMA-CARBOXYGLUTAMATE
• CONJUGATE ADDITION
• MANNICH REACTION
• OXAZOLONES
• PEPTIDE
• CATALYSIS
• ANALOGS

A convenient and functional-group-tolerant organocatalytic asymmetric 1,4-addition of azlactones and dehydroalanine is disclosed. The reaction is used for the first synthesis of chiral alpha,gamma-diamino diacid derivatives with nonadjacent stereogenic centers in moderate to high yields, with excellent diastereo- and enantioselectivities, under the catalysis of a chiral thiourea catalyst. In addition, the reaction could be conducted in gram-scale, and the products of the reaction could be readily converted to various alpha,gamma-diamino diacid derivatives, alpha,gamma-diamino dialcohols, and modified peptides with nonproteinogenic amino acid residues.

• 出版日期2018-11-16
• 单位中山大学; 兰州大学