Journal article
Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid
I Tirotta, NL Fifer, J Eakins, CA Hutton
Tetrahedron Letters | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2013
Abstract
The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazolidinone products can be optimized through a judicious choice of Lewis acid and N-protecting group. © 2012 Elsevier Ltd. All rights reserved.
Grants
Awarded by Australian Research Council
Funding Acknowledgements
Financial support from the Australian Research Council (DP110100112) is acknowledged.