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The Krische allylation involves the enantioselective iridium-catalyzed addition of an allyl group to an aldehyde or an alcohol, resulting in the formation of a secondary homoallylic alcohol.[1][2] The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using aldehyde reactants, hydrogen transfer from 2-propanol. Unlike other allylation methods, the Krische allylation avoids the use of preformed allyl metal reagents and enables the direct conversion of primary alcohols to secondary homoallylic alcohols (precluding alcohol to aldehyde oxidation).[1][3]
- ^ a b Kim, In Su; Ngai, Ming-Yu; Krische, Michael J. (2008-11-05). "Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition". Journal of the American Chemical Society. 130 (44): 14891–14899. doi:10.1021/ja805722e. ISSN 0002-7863. PMC 2890235. PMID 18841896.
- ^ Strategies and Tactics in Organic Synthesis, Volume 10 Michael Harmata Ed.
- ^ Feng, Jiajie; Kasun, Zachary A.; Krische, Michael J. (2016-05-04). "Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis". Journal of the American Chemical Society. 138 (17): 5467–5478. doi:10.1021/jacs.6b02019. ISSN 0002-7863. PMC 4871165. PMID 27113543.