期刊
ACS CATALYSIS
卷 6, 期 10, 页码 6473-6477出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01962
关键词
asymmetric catalysis; dearomatization; indole; organocatalysis; pyridines
资金
- University of Bologna (RFO program)
The catalytic enantioselective dearomatization of pyridines with nucleophiles represents a direct and convenient access to highly valuable dihydropyridines. Available methods, mostly based on N-acylpyridinium salts, give addition to the C-2/C-6 of the pyridine nucleus, rendering 1,2-/1,6-dihydropyridines. Herein, we present an alternative approach to this type of dearomatization reaction, employing activated N-benzylpyridinium salts in combination with a bifunctional organic catalyst. Optically active 1,4-dihydropyridines resulting from the addition of the nucleophile (indole) to the C-4 of the pyridine nucleus are obtained as major products, rendering this method for nucleophilic dearomatization of pyridines complementary to previous approaches.
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