A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.
AUTHORS
Senter
TJ ,
O'Reilly
MC ,
Chong
KM ,
Sulikowski
GA ,
Lindsley
CW ,
. Tetrahedron letters. 2015 3 4; 56(10). 1276-1279
- PMID: 26834294 [PubMed].
- PMCID: PMC4730893.
- NIHMSID: NIHMS662286
ABSTRACT
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).
Tags: 2015