cheminform abstract: imino-diels—alder reactions of 1-aryl-3-(trialkylsiloxy)-1,3-butadienes in...

ChemInform 2008, 39, issue 50 © 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de Pyridine derivatives R 0380 Imino-Diels—Alder Reactions of 1-Aryl-3-(trialkylsiloxy)-1,3-butadienes in Solu- tion and the Solid Phase. — Cycloaddition of arylbutadienes (I) with glyoxylate-de- rived imine (II) to afford tetrahydropyridines (III)/(IV) is studied. The reaction pro- ceeds with high trans-diastereoselectivity for electron-rich arylbutadienes but with low diastereoselectivity for the corresponding o-nitroaryl derivatives [cf. (Ia) vs. (Ic)]. The trans-selectivity for the latter can be improved by use of the chiral imine (VII). Sol- id-supported imine dienophiles afford the N-deprotected cycloadducts by direct cleav- age from the resin without any diastereoselectivity. — (CABALLERO*, E.; FIGUEROA, J.; PUEBLA, P.; PELAEZ, R.; TOME, F.; MEDARDE, M.; Eur. J. Org. Chem. 2008, 23, 4004-4014; Dep. Quim. Org. Farm., Fac. Farm., Univ. Salamanca, E-37007 Salamanca, Spain; Eng.) — Mischke 50- 136

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Page 1: ChemInform Abstract: Imino-Diels—Alder Reactions of 1-Aryl-3-(trialkylsiloxy)-1,3-butadienes in Solution and the Solid Phase

www.cheminform.wiley-vch.de

200850.fm Page 150 Monday, November 10, 2008 5:15 PM

Pyridine derivativesR 0380 Imino-Diels—Alder Reactions of 1-Aryl-3-(trialkylsiloxy)-1,3-butadienes in Solu-

tion and the Solid Phase. — Cycloaddition of arylbutadienes (I) with glyoxylate-de-rived imine (II) to afford tetrahydropyridines (III)/(IV) is studied. The reaction pro-ceeds with high trans-diastereoselectivity for electron-rich arylbutadienes but with low diastereoselectivity for the corresponding o-nitroaryl derivatives [cf. (Ia) vs. (Ic)]. The trans-selectivity for the latter can be improved by use of the chiral imine (VII). Sol-id-supported imine dienophiles afford the N-deprotected cycloadducts by direct cleav-age from the resin without any diastereoselectivity. — (CABALLERO*, E.; FIGUEROA, J.; PUEBLA, P.; PELAEZ, R.; TOME, F.; MEDARDE, M.; Eur. J. Org. Chem. 2008, 23, 4004-4014; Dep. Quim. Org. Farm., Fac. Farm., Univ. Salamanca, E-37007 Salamanca, Spain; Eng.) — Mischke

50- 136

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