313. P. Cottet, D. Müller, A. Alexakis,
     “Copper-Catalyzed Asymmetric Conjugate Addition of Alkenyl- and Alkylalanes to α,β-Unsaturated Lactams”
     Org. Lett. 2013, 15, 828-831.

Alkenyl and alkyl groups have been successfully introduced to six-membered α,β-unsaturated lactams via a copper-catalyzed asymmetric 1,4-addition of the corresponding alanes. Moderate to good yields and good to excellent enantioselectivities are achieved by using a combination of the very cheap copper(II) naphthenate and a readily available phosphine amine ligand. The creation of an all-carbon quaternary stereogenic center, via Michael addition to a trisubstituted conjugated lactam, is also disclosed for the first time.

DOI : 10.1021/ol303505k 

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