Mono-Chlorination of Electron-Rich Arylalkyl- and Heteroarylalkyl-amines and Amino Acids Using Sulfuryl Chloride

Abstract

Sulfuryl chloride has been used to mono-chlorinate electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids in a mild and efficient one-pot transformation with straightforward purification­. Protection of the amines was not needed, and racemization of the chiral amino acids was minimal.

Key words

halogenation - chlorination - sulfuryl chloride - amino acids - amines

References

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8

Chiral purity (ee%) was determined by chiral HPLC. Specific conditions were: 9 and 10 used Chiralcel OD-H with heptane-i-PrOH-Et₂NH (95:5:0.1) at a flow rate of 0.8 mL/min; 11 and 12 used Chiralpak AD with heptane-i-PrOH-Et₂NH (98:2:0.1) at a flow rate of 1.0 mL/min, 13 and 14 used Chiralpak OJ with heptane-MeOH-EtOH-Et₂NH (85:7.5:7.5:0.1) at a flow rate of 1.0 mL/min; 15 and 16 used Chiralpak AD with heptane-i-PrOH-Et₂NH (95:5:0.1 v/v/v) at a flow rate of 1.0 mL/min.