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. 2010 Sep 24;49(40):7312-5.
doi: 10.1002/anie.201004156.

Catalyst-controlled Wacker-type oxidation of protected allylic amines

Brian W Michel  1 , Jessica R McCombs, Andrea Winkler, Matthew S Sigman
Affiliations

Catalyst-controlled Wacker-type oxidation of protected allylic amines

Brian W Michel et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
a) Allylic phthalimides give high aldehyde selectivity under Tsuji–Wacker conditions, as reported by Feringa and co-workers.[4] b) Proposed intermediate in [Pd(Quinox)]–TBHP catalyst system. c) [Pd(Quinox)]–TBHP represents a catalyst-controlled oxidation system for protected allylic amines. PG = protecting group.
Scheme 2
Scheme 2
a) Examination of the retention of enantiomeric excess and b) comparison to the Tsuji–Wacker oxidation.
Scheme 3
Scheme 3
N-Methyl benzoyl protected allylic amines proved to be a limitation and a mechanistic tool.
Scheme 4
Scheme 4
Diastereoselective reductions to provide both a) anti and b) syn β-amino alcohols.
Scheme 5
Scheme 5
Improved one-pot synthesis of the Quinox ligand.
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References

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