A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds†
Abstract
A [2+2+2] annulation reaction between cyclohexanone, β-nitrostyrene and 2-arylidene-1,3-indanedione afforded multisubstituted spiro trans-decalinol derivatives in high chemical yields (up to 75%) and excellent diastereoselectivity (up to >20 : 1) at room temperature. This one-pot three-component system follows a triple cascade sequence via the Michael/nitro-Michael/Aldol process, resulting in the formation of three C–C bonds, five contiguous stereocenters as well as a spiro quaternary carbon center.