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Updated: Apr 3, 2026
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction
Bhavani Shankar Chinta1, Beeraiah Baire1
1Department of Chemistry, Indian Institute of Technology Madras , Chennai 600036, Tamilnadu India.
Abstract:
A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl-piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step.
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