Asymmetric Synthesis of 2-Aryl-Tetrahydropyrans via Arene Chromium Tricarbonyl Methodology 1: cis-2-Aryl-4-Chloro-Tetrahydropyrans

Article abstract of DOI:10.1016/S0957-4166(00)82002-9

Treatment of acetals derived from ortho substituted benzaldehyde chromium tricarbonyl complexes and methanol with homoallylic alcohol and titanium tetrachloride produces the corresponding (RS,RS,SR,RS)-cis-2-aryl-4-chloro-tetrahydropyran complexes completely diastereoselectively.Thus, by this method, homochiral (R)-(-)-o-anisaldehyde chromium tricarbonyl is converted, after decomplexation, to homochiral (R,S)-(+)-cis-2-o-anisyl-4-chloro-tetrahydropyran.