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Organocatalytic Enantioselective Michael–Michael–Michael–Aldol Condensation Reactions: Control of Five Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Highly Functionalized Hexa­hydro­phenan­threnes

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Figshare2016-02-16 更新2026-04-29 收录
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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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2016-02-16
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