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Updated: Feb 6, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of Chiral Tryptamines via a Regioselective Indole Alkylation
Jens Wolfard1, Jie Xu1, Haiming Zhang1
1Department of Small Molecule Process Chemistry , Genentech, Inc. , 1 DNA Way , South San Francisco , California 94080 , United States.
Abstract:
A practical synthesis of chiral tryptamines from simple, unprotected indoles has been developed. Indole nucleophiles prepared with MeMgCl in the presence of CuCl reacted with chiral cyclic sulfamidates almost exclusively at the C3-position of indole to form a variety of α- and/or β-substituted chiral tryptamines in good yield with excellent regioselectivity. The utility of this simple alkylation process has been demonstrated with the practical synthesis of two biologically active targets, cipargamin and TIK-301, which were completed in three steps, starting from the corresponding indole starting materials.
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