AI Article Synopsis
- The study presents a method for synthesizing β-alkylated secondary alcohols using ruthenium as a catalyst, which involves opening epoxide rings with primary alcohols.
- The reaction not only uses alcohol as the main carbon source but also facilitates a hydrogen transfer process that selectively allows for the formation of desired products.
- The method demonstrated a wide applicability, successfully processing 40 different examples, including drug and natural product derivatives, with strong regioselectivity across various substrates.
Article Abstract
Herein, we report the ruthenium-catalyzed synthesis of β-alkylated secondary alcohols via the regioselective ring-opening of epoxides with feedstock primary alcohols. The reaction utilized alcohol as the carbon source and the terminal reductant. Kinetic and labeling experiments elucidate the hydrogen transfer catalysis that operates via tandem Markovnikov selective transfer hydrogenation of terminal epoxides and hydrogen transfer-mediated cross-coupling of the resulting alcohol with primary alcohol substrates. A broad scope (40 examples including drugs/natural product derivatives) and excellent regioselectivity for a variety of substrates were shown.
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| http://dx.doi.org/10.1021/acs.joc.2c02354 | DOI Listing |
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