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Diastereoselective Synthesis of Nine‐Membered Heterocycles via the Cycloaddition and Sequential Rearrangement of N ‐Vinyl Nitrones with Isocyanates
Author(s) -
Zou Ning,
Jiao JiWen,
Feng Yu,
Chen ChunHua,
Liang Cui,
Su GuiFa,
Mo DongLiang
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700685
Subject(s) - chemistry , cycloaddition , aromatization , isomerization , decarboxylation , rearrangement reaction , organic chemistry , catalysis
A metal‐free construction of highly diastereoselective nine‐membered heterocycles is described via the cycloaddition and rearrangement of N ‐vinyl‐ α,β ‐unsaturated ketonitrones and isocyanates. Notably, the prepared nine‐membered heterocycles afforded 2,3‐dihydropyrrolizines under heating conditions. Mechanistic studies showed that the nine‐membered rings might undergo decarboxylation, isomerization, aza‐Michael addition, and aromatization to afford 2,3‐dihydropyrrolizines in a one‐pot reaction.