Kiran Chinthapally

University of Notre Dame | ND · Department of Chemistry and Biochemistry

A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of...

Recent years have witnessed significant achievements in the field of organic chemistry, which have led to new drugs and the discovery of new and biologically interesting molecules. Herein, we describe a practical and efficient approach to the synthesis of enantiomerically pure and diverse lysobisphosphatidic acid analogues. The key feature of the s...

The Front Cover illustrates a dual catalyst system that minimizes the activation energy to enable new synthetic transformations. Here, a gentleman attempts to pick fruits from a tree; however, his height with a box (representing Rh (II)) is insufficient to reach the fruit. Beside him, a woman attempts to pick fruit – but alas, this box (catalyst II...

An efficient seven-step procedure is described for the synthesis of (25R)-cholesta-5,7-diene-3β,26-diol from commercially available ergosterol in an overall yield of 25%. The synthesis features Julia-Kocienski olefination of the aldehyde with benzothiazole sulfone ester in presence of LiHMDS followed by reduction of the alkene.

Dual catalysis represents an alternative archetype in carbene chemistry that surpasses traditional single metal‐catalyst systems. By employing dual catalyst systems, one can improve the efficiency of existing reactions and enable new chemical transformations. Reactions involving dual synergistic catalysis are increasingly valuable as they offer con...

A rhodium carbenoid initiated cascade has been developed for the stereoselective synthesis of medium-sized azacycles. The cascade approach utilizes readily accessible N-benzyl protected aminochalcones and vinyldiazo compounds to access 9-membered azacycles through a carbene- nitrogen insertion/aldol/oxy-Cope sequence. The cascade reaction has prove...

A Rh(II)/Au(I) catalyzed carbene cascade approach for the stereoselective synthesis of diverse spirocarbocycles is described. The cascade reaction involves a rhodium carbene initiated sp2 C–H functionalization followed by a gold catalyzed Conia‐ene cyclization. The cascade reaction accommodates a variety of aryl substituents as well as ring sizes a...

A serendipitous five-step cascade of rhodium vinylcarbenoids with aminochalcones enables a unique synthetic approach to highly functionalized tri- and tetra-cyclic quinolines. The cascade reaction begins with the insertion of aminochalcone nitrogen into rhodium vinylcarbenoids followed by an intramolecular aldol cyclization to provide a substituted...

A facile and convergent approach has been developed for the stereoselective construction of biologically important polyhydroxylated 2-acyl indolizidine framework using aza-Cope rearrangement-Mannich cyclization as a key step. The generality of this methodology is demonstrated with various lactol-tosylates derived from carbohydrates. Present method...

The title reaction generally proceeds within a few minutes under mild conditions to provide insertion products in excellent yields.

The cover picture shows O–H insertion reactions of carboxylic acids into highly stabilized acceptor/acceptor diazo compounds. Rh2(esp)2 acts as an effective catalyst for the decomposition of these stable diazo compounds to form a reactive rhodium carbenoid. The carboxylic acid comes into contact with the reactive rhodium carbenoid and undergoes an...

Rh2(esp)2 has been identified as a highly efficient catalyst for O–H insertion of carboxylic acids into acceptor/acceptor diazo compounds. The insertion reaction proceeds in CH2Cl2 within minutes at room temperature in excellent yields and accommodates carboxylic acids having varying functionalities including amino acids, free alcoholic and phenoli...

Lapachol (1), a naphthoquinone isolated mostly from the plants of bignoniaceae family has a broad spectrum of biological activities and as a consequence it has been the object of different chemical transformations. Lomatiol (3), another naturally occurring naphthoquinone having structural similarities to lapachol, has been obtained from chemical an...

A novel domino synthesis of 1,3,5-trisubstituted hydantoin derivatives has been developed in low melting l-(+)-tartaric acid-DMU melt mixtures. The functionalized hydantoins are obtained in good yields from β,γ-unsaturated ketoacids and urea under environmentally benign and simple reaction conditions.