期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 47, 页码 15113-15121出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201727
关键词
alkyl migration; gold; ketones; regioselectivity; tandem reactions
资金
- National Natural Science Foundation of China [20972054]
- 973 Program [2011CB808600]
- Fok Ying Tung Education Foundation
- Program of Eastern Scholar at Shanghai Institutions of Higher Learning
A series of 2-alkynyl carbonyl compounds that contain a cyclopentene ring or a heterocycle can be transformed into various fused dihydrobenzofurans and tetrahydrofuro[2,3-c]pyridines by means of a 1,2-alkyl migration process. Both of these reactions proceed with excellent regioselectivity and stereospecificity when using a cationic gold(I) catalyst. Treatment of 4-styrylcyclopent-1-enecarboxylates under different conditions affords a range of highly functionalized dihydrobenzofurans and dihydroisobenzofurans. A divergence in product selectivity, which depends on the anion of the silver salts used, was observed. Interestingly, ring-fused tetrahydroquinolines undergo only 1,2'-alkyl migration reaction by means of a C?C cleavage/cyclization sequence to provide tetrahydroazepine derivatives. Mechanistic studies suggest that the gold complexes catalyze 1,2-alkyl migration reactions through a concerted reaction pathway and 1,2'-alkyl migration reactions through a stepwise reaction pathway.
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