Enantioselective Ruthenium-Catalyzed Carbonyl Allylation via Alkyne-Alcohol C-C Bond-Forming Transfer Hydrogenation: Allene Hydrometalation vs Oxidative Coupling

Tao Liang, Khoa D. Nguyen, Wandi Zhang and Michael J. Krische*

*Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States, Email: mkrischemail.utexas.edu

T. Liang, K. D. Ngyuen, W. Zhang, M. J. Krische, J. Am. Chem. Soc., 2015, 137, 3161-3164.

DOI: 10.1021/jacs.5b00747

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Abstract

Chiral ruthenium(II) complexes catalyze a highly regio-, diastereo-, and enantioselective reaction of alkynes with primary alcohols to form homoallylic alcohols. In this enantioselective carbonyl allylation, alkynes serve as allylmetal equivalents.

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Dual Ruthenium-Catalyzed Alkene Isomerization-Hydrogen Auto-Transfer Unlocks Skipped Dienes as Pronucleophiles for Enantioselective Alcohol C-H Allylation

Z. J. Dubey, W. Shen, J. A. Little, M. K. Krische, J. Am. Chem. Soc., 2023, 145, 8576-8582.

Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer

E. Ortiz, J. Z. Shezaf, Y.-H. Chang, T. P. Gonçalves, K.-W. Huang, M. J. Krische, J. Am. Chem. Soc., 2021, 143, 16709-16717.

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Key Words

homoallylic alcohols

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ID: J48-Y2015