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Title: 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. Author: Hong BC, Lin CW, Liao WK, Lee GH. Journal: Org Lett; 2013 Dec 20; 15(24):6258-61. PubMed ID: 24266326. 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.[Abstract] [Full Text] [Related] [New Search]