Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

• Delphine Pichon,
• Jennifer Morvan,
• Christophe Crévisy and
• Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

• accomplished in this stimulating field. Keywords: acylimidazole; N-acyloxazolidinone; N-acylpyrrole; N-acylpyrrolidinone; aldehyde; amide; copper catalysis; electron-deficient alkenes; enantioselective conjugate addition; Michael acceptor; thioester; Introduction Generating high molecular complexity and

• was efficiently converted to highly desirable anti,syn- and anti,anti-3,5,7-(Me,OR,Me)-substituted products 42a/b, which were isolated in good yields and excellent diastereomeric ratios (up to >95:5, Scheme 18). α,β-Unsaturated N-acyloxazolidinone, N-acylpyrrolidinone, and amide derivatives Similar to

• organometallic reagents to Michael acceptors has been extensively studied for many decades and led to remarkable results. However, for a long time, some classes of Michael acceptors (α,β-unsaturated aldehydes, thioesters, acylimidazoles, N-acyloxazolidinone, N-acylpyrrolidinone, amides, N-acylpyrroles) have been