Tandem α‐Alkylation/Asymmetric Transfer Hydrogenation of Acetophenones with Primary Alcohols. Issue 30 (15th September 2014)

• Record Type: Journal Article
• Authors: Kovalenko, Oleksandr O.; Lundberg, Helena; Hübner, Dennis; Adolfsson, Hans
• Is Part Of: European journal of organic chemistry. Issue 30(2014)
• Page Start: 6639
• Page End: 6642
• Publication Date: 2014-09-15
• Subjects: Alkylation -- Amino acids -- Asymmetric catalysis -- Reduction -- Ruthenium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403032
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A tandem α‐alkylation/asymmetric transfer hydrogenation of acetophenones with primary alcohols, mediated by a single ruthenium catalyst, is described. Under optimized reaction conditions and with use of [Ru( p ‐cymene)Cl2 ]2 in combination with an amino acid hydroxyamide ligand, the chiral secondary alcohol products were isolated in moderate yields and in moderate to good enantiomeric excess (up to 89 % ee ). Abstract : One catalyst – one pot – two reactions. Acetophenones are initially alkylated with primary alcohols by the borrowing hydrogen methodology. The alkylation products are directly converted to enantiomerically enriched secondary alcohols.