2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions

Luke D. Elliott, Joe W. Wrigglesworth, Brian Cox, Guy C. Lloyd-Jones, Kevin I. Booker-Milbum

Research output: Contribution to journalArticle (Academic Journal)peer-review

34 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)728-731
Number of pages4
JournalOrganic Letters
Volume13
Issue number4
DOIs
Publication statusPublished - 18 Feb 2011

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