- Senter TJ, O'Reilly MC, Chong KM, Sulikowski GA, Lindsley CW. A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis. Tetrahedron letters. 2015 Mar 4;56(10). 1276-1279. PMID: 26834294 [PubMed]. PMCID: PMC4730893. NIHMSID: NIHMS662286.
A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).