[reaction: see text] Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using (i)PrOH as the reducing agent. A high degree of cis/trans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by (i)PrOH. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity (68-80% ee) was observed.
Efficient and practical: An aluminum‐based catalyst system for the asymmetric Meerwein–Schmidt–Ponndorf–Verley reduction of aromatic ketones is reported. By using iPrOH as the achiral hydride source and BINOL‐type chiral ligands (see scheme), chiral secondary aromatic alcohols (up to 83 % ee) can be obtained in good yields.
[reaction: see text] Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC.AlEt(3) complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.
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