Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes

Abstract

Ru-catalyzed synthesis of mixed alkyl-alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl 2(PPh 3) 3 and [RuCl 2(1,5-COD)] x and phosphines [PPh 3 or P(p-chlorophenyl) 3] or SbPh 3. Of particular importance is the almost quantitative elimination of transacetalization. The addition proceeds through allyl complexes, not via isomerization of allyl ethers - subsequent addition of ROH to vinyl ethers. © The Author(s) 2011.