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.
Catalytic Enantioselective Addition of Indoles to Activated N-Benzylpyridinium Salts: Nucleophilic Dearomatization of Pyridines with Unusual C-4 Regioselectivity / Bertuzzi, Giulio; Sinisi, Alessandro; Caruana, Lorenzo; Mazzanti, Andrea; Fochi, Mariafrancesca; Bernardi, Luca. - In: ACS CATALYSIS. - ISSN 2155-5435. - STAMPA. - 6:10(2016), pp. 6473-6477. [10.1021/acscatal.6b01962]
Catalytic Enantioselective Addition of Indoles to Activated N-Benzylpyridinium Salts: Nucleophilic Dearomatization of Pyridines with Unusual C-4 Regioselectivity
BERTUZZI, GIULIO;SINISI, ALESSANDRO;CARUANA, LORENZO;MAZZANTI, ANDREA;FOCHI, MARIAFRANCESCA;BERNARDI, LUCA
2016
Abstract
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.File | Dimensione | Formato | |
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