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Relevant academic research and scientific papers

A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate

Substituted cyclopropenes serve as compact biorthogonal appendages that enable analysis of biomolecules in complex systems. Neurotransmitters, a chemically diverse group of biomolecules that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe the synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate starting from a Garner's aldehyde-derived alkyne. The deprotected cyclopropene glutamate was stable in solution but decomposed upon concentration. Appending a light-cleavable group improved the stability of the cyclopropene while simultaneously caging the neurotransmitter. This strategy has the potential to permit deployment of cyclopropene-modified glutamate as a bioorthogonal probe of the neurotransmitter glutamate in vivo with spatiotemporal precision.

A direct route to 2-alkyl-4-carbethoxy-5-vinyloxazoles

The reaction of an α-chloroglycinate ester with the dimethylaluminum acetylide derivative of phenyl propargyl ether provides the corresponding 5-vinyloxazole in 40-50% yield.

A Peterson avenue to 5-alkenyloxazoles

The TiCl4-promoted Peterson olefination of aldehydes with readily available 5-(trimethylsilyl)methyloxazoles furnishes 5-alkenyloxazoles (mostly E-isomers).

Iterative oxazole assembly via α-chloroglycinates: Total synthesis of (-)-muscoride A

An efificient iterative synthesis of oxazoles involves the cyclization of 2-alkynyl glycinates (see scheme) formed from the reaction of 1-alkynyl aluminum reagents with α-chloroglycinates. This approach was used in the total synthesis of the bisoxazole na

A catalyst that plays multiple roles: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure

(Matrix Presented) We report a new method for the catalytic, asymmetric synthesis of β-substituted aspartic acid derivatives in which the nucleophilic catalyst serves up to four discrete roles in a one-pot procedure: catalytic dehydrohalogenation of acid chlorides to form ketenes; catalytic dehydrohalogenation of α-chloroamines to form the corresponding imines; catalyzed [2 + 2]-cycloaddition to produce intermediate acyl β-lactams; and finally, nucleophilic ring opening to afford optically enriched β-substituted aspartic acids in high enantioselectivity and diastereoselectivity.

Asymmetric catalysis on sequentially-linked columns

We report a catalytic asymmetric reaction process that involves the use of solid-phase reagents and catalysts that constitute the packing of a series of "reaction columns". This process was applied to the catalytic asymmetric synthesis of β-lactams, to yi