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Updated: May 26, 2025
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Borrowing Hydrogen/Chiral Enamine Relay Catalysis Enables Diastereo- and Enantioselective β-C-H Functionalization of
Ming Wai Liaw1,2, Haruka Hirata1, Gong-Feng Zou1
1Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Abstract:
We report herein an unprecedented borrowing hydrogen/chiral enamine relay catalysis strategy that enables a highly efficient enantioselective formal β-alkylation of simple alcohols using electron-deficient alkenes and especially nitroalkenes. A variety of 1,4-difunctional products such as nitro alcohols are readily accessible in one waste-free step from feedstock alcohols in excellent levels of stereoselectivity. It is important to note that the products are formed in much higher diastereoselectivity than the enamine catalysis step alone under identical conditions, highlighting the unique advantage of cascade borrowing hydrogen catalysis in achieving high efficiency, economy, and stereoselectivity.
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