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Asymmetric Ni-Catalyzed Conjugate Allylation of Activated Enones
Joshua Sieber and James Morken
Journal of the American Chemical Society 130 (14), 4978-83 (14 Mar 2008)
Ni(cod)2 catalyzed allylic alkylation of dialkylidene ketone involves oxidative addition of allylboronate and the less sterically hindered olefine of the dialkylidene ketone to nickel, followed by reductive allylic alkylation of the pendant alkene.
 
Allylsilane-Vinylarene Cross-Metathesis Enables a Powerful Approach to Enantioselective Imine Allylation
John D. Huber, Nicholas R. Perl, and James L. Leighton
Angewandte Chemie International Edition 9999 (9999), NA (2008)
Chiral allylsilanes are cross coupled with vinylarenes via cross-metathesis to afford allylsilanes with various substitutents at the distal carbon. These reagents are used in the cinnamylation of imines to afford homoallylic amines in good enantioselectivity. These can be further synthetically functionalized to generate heterocycles such as piperadine.
 
Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch
John Huber and James Leighton
Journal of the American Chemical Society 129 (47), 14552-3 (06 Nov 2007)
Cinnamylation of imine is described; hydroxyaryl group directs silane to imine. Benzyl or phenyl group on imine gives allylated imine in good syn or anti selectivity, respectively, with excellent ee.
 
Development of General Catalytic Allylation of Acylhydrazones with Pinacolyl Allylboronate Using an Indium(I) Catalyst
Uwe Schneider, I-Hon Chen, and Shu Kobayashi
Organic Letters 10 (5), 737-40 (2008)
Various aliphatic aldehyde-derived hyrazones are allylated with a catalytic amount of indium (I) and allylborate to generate hydrazides. Alpha-beta unsaturated hydrazone gives 1,2-addition product exclusively. Methanol is noted to play an important role in converting allylborate with indium iodide into catalytically active species.

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