Multifunctionalized amino acids, especially amino acids with unsaturation, are important, demanding building blocks in peptide chemistry. Here we present a summary of our most recent study using the thio-Claisen rearrangement for the synthesis of anti-β-functionalized γ,δ-unsaturated amino acids. Investigations on scope, limitations, chemoselectivities and stereoselectivities regarding an FeBr 3-catalyzed allylation strategy and a thio-enolate dianion formation strategy for asymmetric thio-Claisen rearrangement are documented. An explanation of the chirality crossover observed between the Eschenmoser-Claisen rearrangement and the thio-Claisen rearrangement is proposed. Novel optically active N α-protected amino acids with biologically interesting functional groups were prepared for the first time.
ASJC Scopus subject areas
- Organic Chemistry
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Liu, Z. (Creator), Mehta, S. J. (Creator), Lee, K. (Creator), Grossman, B. (Creator), Qu, H. (Creator), Gu, X. (Creator), Nichol, G. S. (Creator) & Hruby, V. J. (Creator), Cambridge Crystallographic Data Centre, 2013