Leland Stanford Junior University

Wisconsin Alumni Research Foundation

E.i. Dupont De Nemours and Company

Merck + Co., Inc.

Other

Argonaut Technologies, Inc.

Barry M Trost

Iwao Hachiya

Mark Elliot Wagman

Keith Joseph Kunitsky

Jacques Dumas

Hisanaka Ito

Richard C Bunt

Samuel David Arthur

Nobuyoshi Yasuda

Steven Willis Shuey

Jeffrey W Labadie

Steven M Pitzenberger

Mukesh C Shah

Yonghan Hu

David Alan Conlon

Michael Palucki

David Lee Van Vranken

Francisco Dean Toste

John Anthony Porco, Jr

Javier Ariza Piquer

Peter Bing

Joann M Um

Lewis L McKellip

Thomas R Verhoeven

Yoshinao Tamaru

John E Vincent

Ernest John McEachern

A method is provided for the thermal decarboxylation of a phenolic substrate in the presence of a non-amine basic catalyst to produce a vinyl monomer. The product of the decarboxylation reaction may additionally be acetylated in the presence of an acetylating agent in the same reaction vessel.

Method for preparing hydroxystyrenes and acetylated derivatives thereof

A method for preparing p-(2-hydroxyalkyloxy)styrene monomers and oligomers is described. The method comprises a base-catalyzed reaction of a styrene ester, a suitable alcohol and an alkylene oxide in a single vessel reaction. In this method, the reactive p-hydroxystyrene is generated in situ via the base-catalyzed transesterification reaction between the styrene ester and the alcohol in the presence of the base catalyst. The p-hydroxystyrene formed reacts with the alkylene oxide to form the p-(2-hydroxyalkyloxy)styrene monomer or oligomer.

Method for preparing para-(2-hydroxyalkyloxy) styrene monomers and oligomers

Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates. Such compositions provide a versatile and low-cost alternative to existing catalysts.

Catalytic compositions and methods for asymmetric allylic alkylation

Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.

Catalytic compositions and methods for asymmetric aldol reactions

Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.

Processes are disclosed for preparing 3-hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists. A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo&lsqb;3.1.0&rsqb;hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu&equals;the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo&lsqb;3.1.0&rsqb;hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.

Process for preparing 3-hydroxymethyl-4-(aryl or heterocyclic)-cyclopentanones

Nucleophilic oxygen species, such as primary alcohols, carboxylates, and water, are added to vinyl epoxides in a highly regioselective and enantioselective manner, providing a convenient route to enantiomerically enriched 1,2-diols and oxygen-containing heterocycles. The reaction employs a chiral Pd(0) complex and a borane or borate as co-catalysts Also described are similar additions of nitrogen nucleophiles, and the addition of carbonates to vinyl epoxides using a chiral Pd(0) catalyst.

Palladium and boron co-catalyzed addition of oxygen nucleophiles to vinyl epoxides

A modified solid support for use in solid phase synthesis which comprises: a solid support having a linker group extending therefrom having the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, alkoxy, aryloxy, fluorine, chlorine, iodine and bromine.

Compositions for organic synthesis on solid phase and methods of using

Compositions and methods for the preparation of enantiomerically enriched .alpha.,.alpha.-disubstituted amino acid precursors are presented. Briefly, allylic electrophiles are alkylated with oxazolones in the presence of a base and catalytic quantities of a transition metal complex incorporating a chiral phosphine ligand to yield 4,4-disubstituted-5(4H)-oxazolones. These precursors may be subsequently transformed either synthetically or enzymatically to yield enantiomerically enriched .alpha.,.alpha.-disubstituted amino acids.

Enantiomerically enriched .alpha.,.alpha.-distributed amino acids and

A novel ligand having the Formula 1 structure has proved remarkably successful in the amination of butadiene monoepoxide, which is a potentially desirable substrate for an asymmetric synthesis providing access to each enantiomer of vinylglycinol. ##STR1## This and other ligands described are useful for chiral induction of bond forming reactions with an epoxide substrate.

Asymmetric ligands useful for transition metal catalyzed bond forming

A method for extracting mint oil from mint plants, the method includes applying a surfactant on the plant material and subjecting the plant material to steam distillation.

Method for extraction of essential oils from plant material

Ligands useful for transition metal catalyzed bond forming reactions are provided with a metal binding portion having at least one metal binding moiety ##STR1## wherein Ar and Ar' each is an aryl or a heteroaryl. These ligands may be prepared by providing an aromatic carboxylic acid having a diarylphosphino or diheteroarylphosphino substituent on the aromatic ring, and forming an ester or an amide derivative of the carboxylic acid by coupling with a chiral diol or a chiral diamine. The ligands facilitate, for example, flexible strategies for enantiocontrolled construction of five membered carbocyclic rings with varying substitution patterns and high enantioselectivity.

Growing community of inventors

Los Altos, CA, United States of America

Barry M Trost