Helvetica chimica acta

Asymmetric Diels??Alder Cycloadditions with Chiral Carbamoyl Dienophiles

A Defoin, A Brouillard??Poichet…

Index: Defoin, Albert; Brouillard-Poichet, Agnes; Streith, Jacques Helvetica Chimica Acta, 1992 , vol. 75, # 1 p. 109 - 123

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Citation Number: 29

Abstract

Abstract 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 de 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 ...