Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

(±)-Methyl 1,1a,2,7b-Tetrahydro-2-oxocyclopropa[c] Chromene-1a-carboxylate

“…And this scaffold serves as key intermediates for many useful organic syntheses because of its unique combination of reactivity and structural properties [1][2][3].Consequently, a considerable attention has been directed towards the stereoselective construction of these three-membered carbocyclic ring systems over the past few decades [4]. Recently, among diverse cyclopropane compounds, donor-acceptor (D-A) cyclopropane has attracted many organic chemists due to its special character containing donor and acceptor substituents at vicinal positions [5,6].…”

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

“…[1][2][3] Several such amino acids have been made accessible [4,5] from our previously developed alkyl 2-chloro-2-cyclopropylideneacetates 1-R. [6,7] Although this type of multifunctional building block may be quite convenient, especially for the preparation of β-functionalized amino acids, a more convergent access to cyclopropyl-containing α-amino acids ought to be achievable from modified 2-cyclopropylideneacetates of type 2 already containing a protected amino group adjacent to the carboxylic acid functionality. Here we report a convenient preparation of methyl (2-benzyloxycarbonylamino)cyclopropylideneacetate (2) (Scheme 1) and some of its versatile transformations.…”

Asymmetric Synthesis of (1S,2R)-1-Amino-2-methylcyclopropanephosphonic Acid: A Phosphonic Analogue of (–)-Norcoronamic Acid – Influence of Stereochemistry on Regioselectivity in Sulfoxide–Metal Exchange

“…A conformational constrain is often used in selective ligands design, since constrained amino acids can closely mimic the bioactive conformation of natural neurotransmitters. 3 As a part of our continuing interest in the synthesis of phosphonic analogues of biologically active compounds, 4 we concentrated our studies on phosphonocyclopropylamino acids, compounds combining both properties: conformational restriction and isosteric replacement of carboxylic moiety. Our general approach to this type of structure is based on an asymmetric cyclopropanation of vinylphosphonates using enantiomerically pure (S)-dimethylsulfonium(p-tolylsulfinyl)methylide (1, Figure 1), which we have previously disclosed.…”