Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer?

Chemical Communications Pub Date: 2019-01-04 DOI: 10.1039/C8CC09706B

Abstract

Highly enantioselective iridium catalyzed carbonyl (2-vinyl)allylation or “isoprenylation” is achieved via hydrogen auto-transfer or 2-propanol-mediated reductive coupling from primary alcohol or aldehyde reactants, respectively. Using this method, asymmetric total syntheses of the terpenoid natural products (+)-ipsenol and (+)-ipsdienol were achieved.

Graphical abstract: Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer
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