Asymmetric synthesis of 2-aryl-tetrahydropyrans via arene chromium tricarbonyl methodology 2: 2-Aryl-3-ethyl-4-chloro-tetrahydropyrans
摘要:
Treatment of acetals derived from omicron-tolualdehyde chromium tricarbonyl and omicron-anisaldehyde chromium tricarbonyl with Z- and E-hex-3-en-1-ol and titanium tetrachloride generated, after decomplexation, completely stereoselectively the corresponding r-2-omicron-aryl-c-3-ethyl-c-4-chloro-tetrahydropyrans and r-2-omicron-aryl-t-3-ethyl-c-4-chloro-tetrahydropyrans respectively. This methodology was applied to the asymmetric synthesis of homochiral (R,R,S)- and (S,R,R)-2-omicron-anisyl-3-ethyl-4-chloro-tetrahydropyran from homochiral omicron-anisaldehyde chromium tricarbonyl and Z- and E-hex-3-en-1-ol respectively.