Bicyclic methylene aziridines and reactions thereof
AssigneeWisconsin Alumni Research Foundation
InventorsJennifer SCHOMAKER, Luke BORALSKY, John HERSHBERGER, Jared RIGOLI, Christopher S. ADAMS
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Abstract
The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.
Claims20
A method comprising forming a bicyclic methylene aziridine by an intramolecular allene aziridination reaction;
- wherein an allene group is tethered to an —NH2 group, and the amino group is separated from the proximal allene carbon by 3, 4, 5, or 6 atoms linearly;
- the method comprising combining the allene, an effective rhodium catalyst, a solvent, and an oxidant, to provide a reaction mixture, thereby initiating an intramolecular allene aziridination reaction, to provide a bicyclic methylene aziridine.
A method comprising forming a bicyclic an N,N-aminal, the method comprising forming a bicyclic methylene aziridine by an intramolecular allene aziridination reaction;
- wherein an allene group is tethered to an —NH2 group, and the amino group is separated from the proximal allene carbon by 3, 4, 5, or 6 atoms linearly;
- the method comprising combining the allene, a rhodium catalyst, a solvent, and an oxidant, to provide a reaction mixture, thereby initiating an intramolecular allene aziridination reaction, to provide a bicyclic methylene aziridine;
- contacting the bicyclic methylene aziridine with a nitrene equivalent in the presence of an oxidant to provide an N,N-spiroaminal;
- and
- contacting the N,N-spiroaminal with a nucleophile to provide a bicyclic ring opened nucleophile-addition product.
Dependencies are inferred from the claim text.