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2,2-Difunctionalization of alkenes via Pd(II)-catalyzed Aza-Wacker reactions
journal contribution
posted on 2023-06-08, 19:29 authored by Luke D Elliott, Joe W Wrigglesworth, Brian Cox, Guy C Lloyd-Jones, Kevin I Booker-MilburnN-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-l-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.
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Publication status
- Published
Journal
Organic LettersISSN
1523-7060Publisher
American Chemical SocietyExternal DOI
Issue
4Volume
13Page range
728-731Department affiliated with
- Chemistry Publications
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- No
Peer reviewed?
- Yes
Legacy Posted Date
2015-01-12Usage metrics
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