A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis

TETRAHEDRON LETTERS

卷:56

Article

Senter, Timothy J.¹  O'Reilly, Matthew C.¹  Chong, Katherine M.¹  Sulikowski, Gary A.¹  Lindsley, Craig W.^1,2 

[1] Vanderbilt Univ, Vanderbitl Inst Chem Biol, Dept Chem, Nashville, TN 37232 USA

[2] Vanderbilt Univ, Dept Pharmacol, Vanderbilt Ctr Neurosci Drug Discovety, Nashville, TN 37232 USA

关键词: Organocatalysis;    Azetidine;    Aziridine;    Enantioselective;   

DOI  :  10.1016/j.tetlet.2015.01.140

来源: Elsevier

【 摘 要 】

A short, high-yielding protocol involving the enantioselective alpha-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). (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free