Beilstein J. Org. Chem.2009,5, No. 5, doi:10.3762/bjoc.5.5
Andreas A. Grauer Burkhard Konig Institute for Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93040 Regensburg, Germany 10.3762/bjoc.5.5 Abstract Cα-Tetrasubstitutedα-aminoacids are important building blocks for the synthesis of peptidemimetics with stabilized secondary
aldehydes are prone to give aldol products under the reaction conditions used, we were able to obtain the target cyclic amino acids in low to moderate yields and in some cases with good diastereoselectivity.
Keywords: amino acid synthesis; Cα-tetrasubstitutedα-aminoacids; unnatural amino acids
oligopeptides of natural amino acids are often not suitable for structural studies, as drug candidates or as biological probes. One way to restrict the conformation and introduce rigidity is the use of Cα-tetrasubstitutedα-aminoacids, in which the α-hydrogen atom of the α-amino acid is replaced by an alkyl or
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Graphical Abstract
Figure 1:
Proposed reaction mechanism for the formation of Cα-tetrasubstituted tetrahydrofuran α-amino acids.