Bicyclic methylene aziridines and reactions thereof
AssigneeWisconsin Alumi 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.
Claims17
A method of forming a bicyclic methylene aziridine by an intramolecular allene aziridination reaction, the method comprising:
- combining an 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 having a structure as shown in Formula II:
- wherein
- R1 and R2 are each independently H, alkyl, cycloalkyl, aryl, heteroaryl, heterocycle, (alkyl)cycloalkyl, (alkyl)aryl, (alkyl)heteroaryl, or (alkyl)heterocycle;
- n is 0, 1, or 2;
- Y is —C(═O)— or —S(═O)2—;
- and
- each Z is independently —(CH2)—, —(CHR1), or —(C(R1)2)—;
- and
- wherein the allene comprises an allene group tethered to an amino group (—NH2), and the amino group is separated from the nearest carbon atom of the allene group by 3, 4, 5, or 6 atoms linearly.
Dependencies are inferred from the claim text.