Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 57, Pages 12912-12926Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001253
Keywords
amines; asymmetric; enantioselective; enolates; hydrogen borrowing
Categories
Funding
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- Clarendon Fund
- University College, Oxford
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Hydrogen-borrowing catalysis represents a powerful method for the alkylation of amine or enolate nucleophiles with non-activated alcohols. This approach relies upon a catalyst that can mediate a strategic series of redox events, enabling the formation of C-C and C-N bonds and producing water as the sole by-product. In the majority of cases these reactions have been employed to target achiral or racemic products. In contrast, the focus of this Minireview is upon hydrogen-borrowing-catalysed reactions in which the absolute stereochemical outcome of the process can be controlled. Asymmetric hydrogen-borrowing catalysis is rapidly emerging as a powerful approach for the synthesis of enantioenriched amine and carbonyl containing products and examples involving both C-N and C-C bond formation are presented. A variety of different approaches are discussed including use of chiral auxiliaries, asymmetric catalysis and enantiospecific processes.
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