2,2-Difunctionalization of alkenes via Pd(II)-catalyzed Aza-Wacker reactions

Elliott, Luke D, Wrigglesworth, Joe W, Cox, Brian, Lloyd-Jones, Guy C and Booker-Milburn, Kevin I (2011) 2,2-Difunctionalization of alkenes via Pd(II)-catalyzed Aza-Wacker reactions. Organic Letters, 13 (4). pp. 728-731. ISSN 1523-7060

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N-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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Tom Gittoes
Date Deposited: 12 Jan 2015 15:30
Last Modified: 12 Jan 2015 15:30
URI: http://srodev.sussex.ac.uk/id/eprint/52050
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