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Ag-Catalyzed Diastereo- and Enantioselective Synthesis of beta-Substituted Tryptophans from Sulfonylindoles

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Organic Letters (Impact Factor: 6.32). 03/2010; 12(8):1688-91. DOI: 10.1021/ol100161n
Source: PubMed

ABSTRACT The asymmetric catalytic synthesis of beta-substituted tryptophan derivatives was realized in high diastereo- and enantioselectivity by the reaction of glycine derivatives with sulfonylindoles in the presence of catalyst derived from AgCl and a commercially available chiral monodentate phosphoramidite ligand. The resulting adduct was readily converted to beta-substituted tryptophan in 95% overall yield for two steps, which presented a highly efficient route to chiral beta-substituted tryptophan.

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