d-Isomannide in synthesis: asymmetric Diels–Alder reactions with novel homochiral bis-imine Cu 2+-catalysts

…, K Vandyck, E Van der Eycken, J Van der Eycken…

Index: De Coster, Gert; Vandyck, Koen; Van der Eycken, Erik; Van der Eycken, Johan; Elseviers, Myriam; Roeper, Harald Tetrahedron Asymmetry, 2002 , vol. 13, # 15 p. 1673 - 1679

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Citation Number: 29

Abstract

Herein, we wish to report on the synthesis of homochiral ligands of the type 4 and their use in the Cu 2+ -catalyzed asymmetric Diels–Alder reaction of cyclopentadiene and N-tert-crotonoyloxazolidinone 1 (Scheme 1). For these catalysts, an efficient chirality transfer was anticipated because of their rather rigid conformation and the presence of a C 2 -symmetry axis, reducing the number of possible diastereomeric complexes. ... Reagents and conditions: cyclopentadiene, CuX2, chiral ...