Sulfoxide-Based Functionalization of Tryptophan Derivatives through Sulfenylation and Selenylation
Man Jiang1,2, Wan-Zhen Li1, Yu Luo1
1Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Ave, Yongchuan, Chongqing 402160, P. R. China.
None:
A sulfoxide-based modification of tryptophan derivatives has been established through sulfenylation and selenylation, affording various highly functionalized tryptophan derivatives of great interest in acceptable-to-good yields. Sequential sulfenylation and bromination occur at the C2 and C6 positions of tryptophan derivatives, respectively, under an AcBr/TMSO/thiol reaction system. In contrast, only selenylation can be realized at the C2 position of tryptophan derivatives by the use of AcCl/DMSO and RSeSeR.
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