Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications.

Journal article

[Structure: see text] For the first time, unmodified ynones were used in organocatalytic asymmetric aldol reactions delivering monoprotected anti-alpha,beta-dihydroxyynones in high yields, dr's up to 19:1, and ee's up to 95%. These products can be either reduced to afford enantioenriched unsaturated anti,anti-triol or cyclized using a novel intramolecular phosphine-catalyzed alpha-addition to the ynone. This organocatalytic sequential aldol-cyclization process provides a concise entry to unusual enantioenriched oxygenated heterocycles, which can be used for subsequent structural manipulations.

Authors: Silva, F; Sawicki, M; Gouverneur, V

• Publication status: Published
• Journal: Organic letters
• Volume: 8
• Issue: 23
• Pages: 5417-5419
• Publication date: 2006-11-01
• DOI: 10.1021/ol0624225
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English