An Investigation of the Asymmetric Huisgen %26apos;Click%26apos; Reaction

作者:Stephenson G Richard*; Buttress James P; Deschamps Damien; Lancelot Melanie; Martin James P; Sheldon Alexander I G; Alayrac Carole; Gaumont Annie Claude; Page Philip C Bulman
来源:Synlett, 2013, 24(20): 2723-2729.
DOI:10.1055/s-0033-1340152

摘要

The preparation of a series of new prochiral bis-alkynes is reported. A selection of chiral ligands is examined to gain additional information about the scope of the new asymmetric Huisgen click%26apos; reaction [the desymmetrisation of bis-alkynes using chiral ligands in conjunction with the widely applied copper-catalysed azide-alkyne cycloaddition (CuAAC) triazole synthesis]. The development of a new chiral assay for (+/-)-methyl 2-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-2-cyanopent-4-ynoate, and the production of this mono-triazole in up to 18% enantiomeric excess is described.

  • 出版日期2013-12-17