Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

doi:10.1002/EJOC.200800817

Paper

Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

Published Mar 1, 2009 · Michael Limbach, A. Lygin, M. Es-Sayed*

European Journal of Organic Chemistry

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6

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Abstract

Methyl 2-(benzyloxycarbonylamino)-2-cyclopropylideneacetate (2) was prepared in nine steps starting from L-serine in an overall yield of 24 %. It has been demonstrated to be reasonably reactive in Michael additions of various nucleophiles (6 examples, 75–98 % yields) as well as Diels–Alder reactions, both leading to new cyclopropyl-containing amino acids in protected form. An application of 2 in the synthesis of methyl 4-tert-butoxycarbonylmethyl-5-oxo-4,7-diazaspiro[2.5]octane-8-carboxylate (15), a precursor for geometrically constrained bicyclic peptidomimetics of type 16, has also been proved.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Study Snapshot

Methyl 2-(benzyloxycarbonylamino)-2-cyclopropylideneacetate is a versatile building block for synthesis of cyclopropyl-containing amino acids, with potential applications in geometrically constrained bicyclic peptidomimetics.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Methyl 2‐(Benzyloxycarbonylamino)‐2‐cyclopropylideneacetate: A Versatile Building Block for Cyclopropyl‐Containing Amino Acids

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