Sequential Asymmetric Catalysis in Michael–Michael–Michael–Aldol Reactions: Merging Organocatalysis with Photoredox Catalysis in a One-Pot Enantioselective Synthesis of Highly Functionalized Decalines Bearing a Quaternary Carbon Stereocenter
Organic Letters2013Vol. 15(24), pp. 6258–6261
Citations Over TimeTop 10% of 2013 papers
Abstract
An expedited method has been developed for the enantioselective synthesis of highly functionalized decaline systems containing seven contiguous stereogenic centers with high enantioselectivities (>99% ee). The one-pot methodology comprises a cascade of organocatalytic double Michael-photocatalyzed Michael-aldol reactions of ethyl 2-bromo-6-formylhex-2-enoate, β-alkyl-α,β-unsaturated aldehydes, and α-alkyl-α,β-unsaturated aldehydes. The structure and absolute configuration of an appropriate product were confirmed by X-ray analysis.
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