Synthesis and diastereoselective Diels-Alder reactions of homochiral C2-symmetric butane-1,2-diacetal-based 1,3-dienes

The C-2-symmetric, butane diacetal (BDA) auxiliary-based dienes 2 and 3 are described, which display moderate to excellent diastereoselectivities in Diels-Alder reactions with a range of dienophiles under thermal and Lewis acid-catalysed conditions. (c) 2009 Elsevier Ltd. All rights reserved.