A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds
Poorna Chandrasekhar Settipalli1, Shaik Anwar1
1Deparment of Chemistry, School of Applied Sciences and Humanities, Vignan's Foundation for Science Technology and Research-VFSTR (Deemed to be University), Vadlamudi-522 213, Guntur, Andhra Pradesh, India. shaikanwarcu@gmail.com.
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.
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