Tetrahedron Asymmetry p. 2643 - 2646 (1999)
Update date:2022-08-11
Topics:
Cuesta, Javier
Arsequell, Gemma
Valencia, Gregorio
Gonzalez, Asensio
A visible light-induced desulfurization process for thiols and disulfides using triethylphosphite and triethylborane is reported. The reaction can be effected on a range of organic molecules having either primary, secondary or tertiary thiol groups and disulfides without the need of protecting groups. Thus, after treating L-cystine 7, L-cystine dimethylester 8, thioctic amide 9 and glutathione disulfide 10, first with tributylphosphine, later with triethylborane/triethylphosphite under irradiation in a one-pot reaction, the corresponding desulfurized compounds L-Ala, L-Ala, 1-octanamide and γ-L-Glu-L-Ala-Gly, respectively, are prepared in high yields with retention of configuration.
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