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Updated: Jul 13, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation
Yannick Linne1, Daniel Lücke1, Kjeld Gerdes1
1Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, 30167, Hannover, Germany.
Abstract:
Allylic alcohols are a privileged motif in natural product synthesis and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that chiral acetonide-protected polyketide fragments performing the Hoppe-Matteson-Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities rendering this protocol a highly valuable alternative to the Nozaki-Hiyama-Takai-Kishi reaction. Various stereodyads and -triads were investigated to determine their substrate induction. The mostly strong inherent stereoinduction was attributed to a combination of steric and electronic effects.
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