Concepedia

Unique Ionic Iodine Atom Transfer Cyclization:  A New Route to Iodomethylated Pyrrolidine Derivatives from γ-Iodoolefin and Chloramine-T

Satoshi Minakata, Daisuke Kano, Yoji Oderaotoshi, Mitsuo Komatsu

Organic Letters · 2002 · 35 citations · 14 references

DOI

Concepts

Abstract

[reaction: see text] Pyrrolidines and bicyclic pyrrolidine derivatives can effectively be synthesized from gamma-iodoolefins using commercially available chloramine-T (CT) as a nitrogen source. The cyclization proceeds with high stereoselectivity via a cyclic iodonium intermediate.

References

14

<i>N</i>‐Halocarbamate Salts Lead to More Efficient Catalytic Asymmetric Aminohydroxylation

Guigen Li, Hubert Angert, K. Barry Sharpless · Angewandte Chemie International Edition in English · 1996 · 195 citations

, , +10

Iodine-catalyzed aziridination of alkenes using Chloramine-T as a nitrogen source

Takeya Ando, Daisuke Kano, Satoshi Minakata et al. · Tetrahedron · 1998 · 166 citations

, , +13

A Simple Copper Catalyst for Both Aziridination of Alkenes and Amination of Activated Hydrocarbons with Chloramine-T Trihydrate

David P. Albone, Pavandeep S. Aujla, Paul C. Taylor et al. · The Journal of Organic Chemistry · 1998 · 153 citations

, , +9

Smaller Substituents on Nitrogen Facilitate the Osmium‐Catalyzed Asymmetric Aminohydroxylation

Joachim Rudolph, Peter Sennhenn, Cornelis P. Vlaar et al. · Angewandte Chemie International Edition in English · 1996 · 146 citations

, , +10

Theory Rules Out a [2 + 2] Addition of Osmium Tetroxide to Olefins as Initial Step of the Dihydroxylation Reaction

Ulrich Pidun, Christian Boehme, Gernot Frenking · Angewandte Chemie International Edition in English · 1996 · 123 citations

, , +13