A reliable synthetic route to fused polycyclic indolines is documented by the development of a stereoselective gold catalyzed cascade cyclization of indole propargylic alcohols.

The base-catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1-disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid-base adduct, [Hbase](+) [MeO-B2 pin2 ](-) favored the formation of 1,2,3-triborylated species from the tertiary allylic alcohols and 1-propargylic cyclohexanol at 90 °C.

Various highly substituted 2,3'-diindolylmethane heterocycles were prepared from propargylic alcohols and indole nucleophiles via a transition metal-catalyzed tandem indole annulation/arylation reaction for the first time. Among the metal catalysts we examined, the most economical copper(I) catalyst provided the highest efficiency. The indole nucleophiles could also be replaced by other electro...

A novel C5-alkylation of oxindoles using alcohols as alkylating agents under acid catalysis is described for the first time. The reactions of various benzylic, allylic and propargylic alcohols are studied to obtain the corresponding 5-substituted oxindoles in good yields.

Hydrozirconation of alkynes with Cp2ZrH(Cl) (Schwartz reagent) generates vinyl zirconium species reliably, stereospecifically, and regioselectively. These organometallic reagents can participate in cross-coupling reactions, conjugate and nucleophilic additions, and can undergo carbonylation and halogenation.1 Hydrozirconation of terminal alkynes often proceeds with >50:1 selectivity to form the...

We report the highly selective assembly of unprecedented eta5-1-methylene-1,2-dihydronaphthalenide ligands from the stoichiometric coupling of a phenyl group and two equivalents of disubstituted propargylic alcohols; in this reaction, tetraphenylborate acts as a phenylating agent.

The concise preparation of 4,4,4-trifluorobut-2-yn-1-ones by the oxidation readily accessible corresponding propargylic alcohols as well their utilization Michael acceptors for construction aromatic and heteroaromatic compounds are reported.

The regioselective gold-catalysed hydration of propargylic alcohols to β-hydroxy ketones can be achieved by diverting the gold-catalysed Meyer-Schuster rearrangement through the addition of a protic additive with a pKa of 7-9 such as p-nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an al...

[formula: see text] Treatment of tertiary propargylic alcohols 13 with 3-diazo-2-butanone 6 and catalytic dirhodium tetraacetate in benzene gave good yields of the diastereomeric allenic hydroxyketones 14, with, in some cases, good diastereocontrol. These products are presumably formed via the [2,3]-sigmatropic rearrangement of an alpha-propargyloxy enol derivative. This reaction has been exten...