140160-63-0Relevant academic research and scientific papers
Asymmetric Diels-Alder Cycloadditions with Chiral Carbamoyl Dienophiles
Defoin, Albert,Brouillard-Poichet, Agnes,Streith, Jacques
, p. 109 - 123 (2007/10/02)
Chiral acylnitroso dienophiles 14, which were obtained from L-proline and from D-mandelic acid, reacted with cyclohexa-1,3-diene to give the expected diastereoisomers 15 and 16 (Scheme 2 and Table 1).The d.e. values for these Diels-Alder reactions were moderate; they are related to the molecular stiffness of the dienophiles.The absolute configuration of the major cycloadducts was interpreted in terms of HOMO/LUMO interactions, the approach being 'endo' and the acylnitroso dienophiles reacting from their s-cis-conformation.
