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Imino‐Diels–Alder Reactions of 1‐Aryl‐3‐(trialkylsiloxy)‐1,3‐butadienes in Solution and the Solid Phase
Author(s) -
Caballero Esther,
Figueroa Javier,
Puebla Pilar,
Peláez Rafael,
Tomé Fernando,
Medarde Manuel
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800284
Subject(s) - imine , chemistry , glyoxylate cycle , aryl , nitro , cleavage (geology) , medicinal chemistry , organic chemistry , stereochemistry , catalysis , enzyme , alkyl , geotechnical engineering , fracture (geology) , engineering
Imino‐Diels–Alder reactions between 1‐aryl‐ or 1‐heteroaryl‐3‐(trialkylsiloxy)‐1,3‐butadienes and imines derived from ethyl glyoxylate have been studied. When an achiral imine was used, the diastereoselectivity depended on the nature of the aryl or heteroaryl system; diastereoselectivities > 90 % were observed with methoxyphenyl or indolyl substituents, but were much lower for nitro substituents. High diastereoselectivities were also achieved if a chiral imine derived from methylbenzylamine was used as the dienophile. Solid‐supported imine dienophiles yielded the N ‐deprotected cycloadducts by direct cleavage from the resin with no diastereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)