D. Enders, Robert Hahn, Iuliana L Atodiresei
Apr 15, 2013
Citations
0
Influential Citations
36
Citations
Journal
Advanced Synthesis & Catalysis
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.