1. Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations.
- Author
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Armstrong, Roly J., Akhtar, Wasim M., Young, Tom A., Duarte, Fernanda, and Donohoe, Timothy J.
- Subjects
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HYDROGEN production , *CREDIT , *IRIDIUM , *CATALYSIS , *ALKYLATION , *ASYMMETRIC synthesis - Abstract
Hydrogen borrowing catalysis serves as a powerful alternative to enolate alkylation, enabling the direct coupling of ketones with unactivated alcohols. However, to date, methods that enable control over the absolute stereochemical outcome of such a process have remained elusive. Here we report a catalytic asymmetric method for the synthesis of enantioenriched cyclohexanes from 1,5‐diols via hydrogen borrowing catalysis. This reaction is mediated by the addition of a chiral iridium(I) complex, which is able to impart high levels of enantioselectivity upon the process. A series of enantioenriched cyclohexanes have been prepared and the mode of enantioinduction has been probed by a combination of experimental and DFT studies. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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