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Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations

2019; Wiley; Volume: 131; Issue: 36 Linguagem: Inglês

10.1002/ange.201907514

1521-3757

Roly J. Armstrong, Wasim M. Akhtar, Tom A. Young, Fernanda Duarte, Timothy J. Donohoe,

Asymmetric Synthesis and Catalysis

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.