期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 11, 页码 7015-7025出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00310
关键词
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A highly efficient method for the one-pot synthesis of ring-fused 5-hydrazino-2-cyclopentenone derivatives is achieved through the catalysis of gold(I). Suitable enynyl acetates are mixed with a dialkylazodicarboxylate in the presence of a gold(I) catalyst to undergo cycloisomerization, hetero-Diels-Alder, and ring-opening reactions, resulting in the target compounds.
A highly efficient, one-pot synthesis of ring-fused 5-hydrazino-2-cyclopentenone derivatives is achieved by a gold(I)-catalyzed cycloisomerization/hetero-Diels-Alder/ring-opening tandem reaction of suitable enynyl acetates. By mixing the latter with a dialkylazodicarboxylate in the presence of a gold(I) catalyst, the 1,3-acyloxy migration/Nazarov cyclization process leads to dienyl acetate intermediates which are trapped by the heterodienophile present in situ. This provides strained intermediates which undergo highly regioselective ring opening by a retro aza-Michael reaction promoted by traces of water, eventually yielding the target compounds. Six- and seven-membered ring-fused cyclopentenones and piperidine- and tetrahydropyran-fused cyclopentenones bearing a pendant hydrazino functionality on a bridgehead carbon atom can be obtained in high yield (68-96%) by this approach.
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