A direct and simple activation of quinolines, without isolating unstable intermediates, or using isolated N,O-acetals in the presence of Lewis or Brønsted acids, is described. The procedure is quite straightforward and allows the addition in a stereoselective manner of different aldehydes to various differently substituted quinolines. The desired products were obtained in 28–76 % yields, with dr values up to 83:17 in favor of the syn isomer, and up to 99 % ee. Studies towards the use of acetaldehyde were also performed with different catalysts and the addition was promoted affording the desired product in 62 % yield with 46 % ee. Finally, deprotection and chemical transformations of the enantioenriched adducts were performed.
Organocatalytic Stereoselective Addition of Aldehydes to Acylquinolinium Ions / Mengozzi, Luca; Gualandi, Andrea; Cozzi, Pier Giorgio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - ELETTRONICO. - 2016:19(2016), pp. 3200-3207. [10.1002/ejoc.201600284]
Organocatalytic Stereoselective Addition of Aldehydes to Acylquinolinium Ions
MENGOZZI, LUCA;GUALANDI, ANDREA;COZZI, PIER GIORGIO
2016
Abstract
A direct and simple activation of quinolines, without isolating unstable intermediates, or using isolated N,O-acetals in the presence of Lewis or Brønsted acids, is described. The procedure is quite straightforward and allows the addition in a stereoselective manner of different aldehydes to various differently substituted quinolines. The desired products were obtained in 28–76 % yields, with dr values up to 83:17 in favor of the syn isomer, and up to 99 % ee. Studies towards the use of acetaldehyde were also performed with different catalysts and the addition was promoted affording the desired product in 62 % yield with 46 % ee. Finally, deprotection and chemical transformations of the enantioenriched adducts were performed.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.