立体选择性制备氮杂环丁烷和吡咯烷。

Diastereoselective preparation of azetidines and pyrrolidines.

机构信息

School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT, United Kingdom.

出版信息

Org Lett. 2010 Nov 5;12(21):5044-7. doi: 10.1021/ol102215e.

PMID:20879778

Abstract

Iodine-mediated cyclization of homoallyl amines at room temperature delivered cis-2,4-azetidine through a 4-exo trig cyclization. Isomerization of iodo-azetidines to cis-pyrrolidines could be achieved by heating, with complete stereocontrol. The relative stereochemistry of the iodo-azetidines and pyrrolidines was confirmed by NMR spectroscopy and X-ray crystallography. Further functionalization was achieved through nucleophilic displacement of iodine to deliver substituted azetidines and pyrrolidines. 1,2,3-Triazole-appended azetidines and pyrrolidines were also prepared.

摘要

碘介导的偕胺室温环化反应通过 4-endo-trig 环化反应得到顺式-2,4-氮杂环丁烷。碘代氮杂环丁烷通过加热可以异构化为顺式吡咯烷，并且具有完全的立体选择性。通过 NMR 光谱和 X 射线晶体学确定了碘代氮杂环丁烷和吡咯烷的相对立体化学。通过亲核取代碘原子可以进一步进行官能团化，得到取代的氮杂环丁烷和吡咯烷。还制备了 1,2,3-三唑取代的氮杂环丁烷和吡咯烷。