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

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.

SUBMITTER: Xiang M 

PROVIDER: S-EPMC6339811 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Xiang Ming M   Luo Guoshun G   Wang Yuankai Y   Krische Michael J MJ  

Chemical communications (Cambridge, England) 20190101 7

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. ...[more]

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