| Abstract: | An organocatalytic nitroalkane‐Michael/Henry reaction sequence to functionalized 1,2,3,4‐tetrahydronaphthalen‐1‐ols is described. Starting from 2‐(nitromethyl)benzaldehyde and nitroalkenes a bifunctional quinine‐based squaramide organocatalyst is used to afford the title compounds in moderate to very good yields (25–84%), high diastereomeric ratios (dr>95:5) after crystallization and good to excellent enantioselectivities of 63–99% ee. Starting from γ‐nitro aldehydes and ketones secondary and tertiary cyclohexanols bearing four stereogenic centers can also be prepared with this Michael/Henry domino reaction. |
