A New, Simple Synthesis of N-Tosyl Pyrrolidines and Piperidines

Abstract

Iodocyclization of unsaturated tosylamides promoted by Oxone^® oxidation of KI afforded, in good yields, N-tosyl iodopyrrolidines and piperidines. A new, simple method for the conversion of alcohols to tosylamides is presented.

Key words

pyrrolidines - piperidines - Oxone^® - iodocyclization - toluenesulfonamides

References

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9

Compound 3 showed [α]_D ²⁴ +4.06 (c 2.15, CH₂Cl₂). This value is comparable with the [α] value of the same tosylamide prepared from commercial (R)-2-octyl amine by reaction with p-toluenesulfonyl chloride {[α]_D ²³ +5.0 (c 1.7, CH₂Cl₂)}.

11

CCDC reference number 292928.