Joaquin Plumet

Derivatives of 7-oxabicyclo[2.2.1]heptane in nature and as useful synthetic intermediates

Keywords: Diels-alder-reaction ; opening metathesis polymerization ; acid-catalyzed ; hydrolysis ; lithium aluminum-hydride ; soybean cyst nematode ; diastereoselective bis-hydroxylation ; thromboxane-a2 receptor ; antagonists ; enantioselective total synthesis ; wagner-meerwein ; rearrangements ; platelet-activating-factor Note: Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland. Ecole Super Phys & Chim Ind, Dept Chim Organ, F-75005 Paris 5, France. Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain. Reference LGSA-ARTICLE-1999-014doi:10.1016/S0040-4020(99)00845-5 Record created on 2005-11-09, modified on 2017-05-12

Stereoselective coupling of ketone and carboxylate enolates

This review summarizes the background and the state of the art of the coupling of the enolates of ketones and carboxylic acid derivatives, focusing on the stereoselectivity of the process. Compared with other synthetic applications of enolates, the stereoselective coupling of these species has been considered less in the literature. Recent developments making use of chiral auxiliaries have put forward the versatility of this procedure for the asymmetric synthesis of 1,4-dicarbonyl compounds.

Methyltriphenylphosphonium iodide catalyzes the addition of trimethylsilyl cyanide to aldehydes

Methyltriphenylphosphonium iodide catalyzes the formation of cyanohydrin trimethylsilyl ethers of aliphatic, aromatic and heterocyclic aldehydes.

Regioselective domino metathesis of 7-oxanorbornene derivatives as a new stereoselective entry into 2,6-dioxabicyclo[4.3.0]nonenes

Abstract Domino metathesis of allyl- and propargyl-(2-endo-7-oxanorborn-5-enyl) ethers with allyl acetate in the presence of Grubbs’ ruthenium catalyst affords stereoselectively substituted cis-fused bicyclic ethers (2,6-dioxabicyclo[4.3.0]non-8-enes).

MAGNESIUM MONOPEROXYPHTALATE : A NEW REAGENT FOR THE OXIDATIVE RING OPENING OF FURANS TO CIS-ENEDIONES

Abstract Ring opening of furans can be accomplished with the title reagent to afford cis -enediones stereospecifically, with great advantages over the hazardous MCPBA.

The Staudinger reaction of imines derived from 7-oxanorbornenone: formation of spiranic oxazinone versus β-lactam rings

The Staudinger reaction of imines derived from 7-oxanorbornenone with 2-alkoxyacetyl chlorides afforded spiro-β-lactams albeit with an unexpected stereochemistry. This was not the case with arylacetic acid chlorides, which gave rise to spiranic oxazinone rings as well as the expected β-lactams.

A novel, general, totally stereoselective one-pot synthesis of cis-3-substituted 4-formylazetidin-2-ones

A general, totally stereoselective one-pot synthesis of cis-3-substituted-4-formylazetidin-2-ones based upon the reaction of acid chlorides and 1,4-bis-(4-methoxyphenyl)-1,4-diazabuta-1,3-diene, as synthetic equivalent of the corresponding unknown α—formylimine, has been developed.

Total synthesis of both enantiomers of 15-oxopuupehenol methylendioxy derivatives

Abstract The total synthesis of both enantiomers of puupehenol and 15-oxopuupehenol as methylenedioxy derivatives is described. The key steps of the synthesis are the regioselective transformation of 10 to and the stereoselective cyclization of 12 to 13.

Regio- and stereospecific synthesis of substituted cyclohexenediols from 7-oxabicyclo[2.2.1]hept-5-en-2-ols and organolithium reagents

Abstract The bridge opening reactions of 7-oxabicyclo[2.2.1]hept-5-en-2-ols,4 and6 with organolithium reagents proceed with complete regio- and stereoselectivity to produce highly functionalized cyclohexene derivatives5 and7, respectively.

A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 1-TETRALONE DERIVATIVES USING A SUZUKI COUPLING-FRIEDEL-CRAFTS ACYLATION SEQUENCE

Abstract The reported 1-tetralone derivatives have been synthesized from arylbromides using as key steps a Suzuki coupling followed by intramolecular Friedel-Crafts acylation.