Issue 74, 2022

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.

Graphical abstract: A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds

Supplementary files

Article information

Article type
Communication
Submitted
27 Jun 2022
Accepted
07 Aug 2022
First published
08 Aug 2022

Chem. Commun., 2022,58, 10400-10403

A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds

P. C. Settipalli and S. Anwar, Chem. Commun., 2022, 58, 10400 DOI: 10.1039/D2CC03562F

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