Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions. Issue 15 (12th April 2019)

• Record Type: Journal Article
• Authors: Vallakati, Ravikrishna; Plotnikov, Abel T.; Altman, Ryan A.
• Is Part Of: Tetrahedron. Volume 75:Issue 15(2019)
• Page Start: 2261
• Page End: 2264
• Publication Date: 2019-04-12
• Subjects: L-tryptophan -- CH borylation -- Deborylative deuteration -- Metal-catalysis -- Deuterium labeling; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.02.054
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Herein, we report a practical synthesis of 2-D- l -tryptophan via sequential Ir-catalyzed CH borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc and methyl ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D- L -Tryptophan is stable in many buffers used for biological studies. Graphical abstract: Image 1