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  • Title: Organocatalytic enantioselective Michael-Michael-Michael-aldol condensation reactions: control of five stereocenters in a quadruple-cascade asymmetric synthesis of highly functionalized hexahydrophenanthrenes.
    Author: Raja A, Hong BC, Lee GH.
    Journal: Org Lett; 2014 Nov 07; 16(21):5756-9. PubMed ID: 25337635.
    Abstract:
    A cascade organocatalysis has been developed for the enantioselective synthesis of a highly functionalized hexahydrophenanthrene-2-carbaldehyde containing five contiguous stereogenic centers with high diastereoselectivity and high enantioselectivity (>99% ee). The one-pot method comprises a cascade of organocatalytic Michael-Michael-Michael-aldol reactions of 2-methyl-1,5-dinitro-3-((E)-2-nitrovinyl)benzene and α,β-unsaturated aldehydes (e.g., cinnamaldehyde). The structure and absolute configuration of a product were confirmed by X-ray analysis of an appropriate derivative.
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