2,2-Difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions |
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Authors: | Elliott Luke D Wrigglesworth Joe W Cox Brian Lloyd-Jones Guy C Booker-Milburn Kevin I |
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Affiliation: | School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. |
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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. |
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