Section 56
Chapter 55,721

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

Hong, B.-C.; Lin, C.-W.; Liao, W.-K.; Lee, G.-H.

Organic Letters 15(24): 6258-6261


ISSN/ISBN: 1523-7052
PMID: 24266326
DOI: 10.1021/ol403113c
Accession: 055720752

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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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