Regioselective Dearomatization of N-Alkylquinolinium and Pyridinium Salts under Morita-Baylis-Hillman Conditions

被引:8
作者
Pareek, Abhishek [1 ]
Kalek, Marcin [1 ]
机构
[1] Univ Warsaw, Ctr New Technol, Banacha 2C, PL-02097 Warsaw, Poland
关键词
C-C coupling; Dearomatization; Heterocycles; Morita-Baylis-Hillman reaction; N-alkylquinolinium salts; Synthetic methods; CATALYZED ENANTIOSELECTIVE ARYLATION; NUCLEOPHILIC DEAROMATIZATION; ASYMMETRIC-SYNTHESIS; DERIVATIVES; ALDEHYDES; CONSTRUCTION; ALKALOIDS; ALKYNES; ESTERS; ROUTE;
D O I
10.1002/adsc.202200429
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Morita-Baylis-Hillman reaction employing N-alkylquinolinium salts as electrophiles has been developed. The reaction is promoted by DBU, which acts both as a catalyst activating the electron-poor olefin as well as a base. The dearomatization occurs regioselectively at the C-2 position, delivering a broad range of alpha-(1,2-dihydroquinolin-2-yl)vinyl esters, ketones, and sulfones. The scope of the transformation has also been extended to N-alkylpyridinium salts. For this class of substrates a presence of at least moderately electron-withdrawing substituent in the ring is necessary to attain good reactivity. In particular, N-alkylpyridinium salts containing an ester group undergo the dearomatization regioselectively at the C-4 position, while nitrile and nitro moieties cause the non-selective formation of products of the C-2 and C-6 additions.
引用
收藏
页码:2846 / 2851
页数:6
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