Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

• Katherine M. Byrd

Beilstein J. Org. Chem. 2015, 11, 530–562, doi:10.3762/bjoc.11.60

• underdeveloped due to their inherently low reactivity. This review highlights the work that has been done on both diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams. Keywords: α,β-unsaturated amides; α,β-unsaturated lactams; conjugate addition

• be easily attached and removed or transformed into a variety of functional groups. Though the utility of chiral auxiliaries in DCA reactions has been demonstrated in α,β-unsaturated amides, this method has not been extensively applied to α,β-unsaturated lactams. Another drawback to this approach is

• ][3][4]. Alkenyl, alkynyl and aryl organometallic reagents have been used less frequently [78][79][80][81][82][83][84]. Feringa and co-workers reported the first copper-catalyzed ECA reactions of α,β-unsaturated lactams in 2004 [22]. They were able to perform these reactions in high yields and

Visible-light-induced, Ir-catalyzed reactions of N-methyl-N-((trimethylsilyl)methyl)aniline with cyclic α,β-unsaturated carbonyl compounds

• Dominik Lenhart and
• Thorsten Bach

Beilstein J. Org. Chem. 2014, 10, 890–896, doi:10.3762/bjoc.10.86

• formation of a tricyclic product. Addition to cyclic α,β-unsaturated lactams Lactams offer the possibility of reactivity tuning by choosing an appropriate protecting group at the nitrogen atom. Since initial experiments with unprotected pyrrolin-2-one were not promising the respective tert-butyloxycarbonyl

• -dihydro-2H-pyran-2-one (12). Ir-catalyzed addition reactions of N-methyl-N-((trimethylsilyl)methyl)aniline (5) to 2-cyclopentenone (15). Ir-catalyzed formation of tricyclic products 19 by a domino radical addition reaction to α,β-unsaturated lactams 18. Ir-catalyzed addition reactions of N-methyl-N