The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Current research in materials has devoted much attention to graphene, with a considerable amount of the chemical manipulation going through the oxidized state of the material, known as graphene oxide (GO). In this report, the hydroxyl functionalities in GO, the vast majority th...

Stereoselectively labeled samples of E—2an Z—[9—2H,3H]— chorismate have been synthesized from Fand z-[3H, Hlphosphoen6lpyruvate by the enzymes of the shikimate pathway. The position of the tritium label at the 9—position of chorismate has been determined, from which it is evident that in the reaction catalyzed by 3-phosphoshikimate 1—carboxyvinyltransferase, the addition step has the opposite s...

Synthesis of novel pyrazole-fused heterocycles, i.e., dihydro-1H- or 2H-oxepino[3,2-c]pyrazoles (6 or 7) from 4-allyloxy-1H-pyrazoles (1) via combination of Claisen rearrangement and ring-closing metathesis (RCM) has been achieved. A suitable catalyst for the RCM of 5-allyl-4-allyloxy-1H-pyrazoles (4) was proved to be the Grubbs second generation catalyst (Grubbs2nd) to give the predicted RCM p...

In the title compound, [Cu(C(17)H(30)N(2)O(2))(C(3)H(7)NO)(2)][SbF(6)](2), which is a potential catalyst in the asymmetric Gosteli-Claisen rearrangement, the Cu atom adopts a distorted cis-CuN(2)O(2) square-planar geometry arising from N,N'-bidentate coordin-ation by the chiral ligand and two O-bonded dimethyl-formamide mol-ecules. Two short C-H⋯O contacts occur within the ligand and two weak i...

Allylic and benzylic alcohols are converted into corresponding unsymmetrical ethers when reacted with various orthoesters in the presence of montmorillonite KSF at ambient temperature. A detailed study has been undertaken to examine the mechanism and generality of these reactions with regard to various acidic catalysts, which reveal interesting competitive reactions mainly O-acetylation, togeth...

The first total synthesis of garsubellin A, a neurotrophic compound with potent choline acetyltransferase-inducing activity, is described. Keys for success were (1) stereoselective intermolecular aldol reaction at the C-4 position with acetaldehyde, (2) stereoelective Claisen rearrangement to introduce an allyl group to the most sterically crowded position at C-6, (3) ring-closing metathesis to...