Brigham Young University

Hoffmann-la Roche Inc.

Bryant E Rossiter

Jerald S Bradshaw

Milton L Lee

Bryon J Tarbet

Karin E Markides

Francois Montavon

Deborah F Johnson

Abdul Malik

Shawn L Reese

Masakatsu Eguchi

Felix Roessler

Cyclodextrin containing polymeric siloxanes wherein the cyclodextrin is connected to the polymeric siloxane by a single linking member connected to the 2, 3 or 6-position of the cyclodextrin are disclosed. These polymers are chemically and thermally stable to gas, supercritical fluid chromatographic conditions. The single arm attachment provides cyclodextrin containing polysiloxane polymers having synthesis reproducibility from batch to batch resulting in consistent chromatographic performance of the resulting chiral phases. The use of such polymers as chiral stationary phases in analytical and preparative gas, supercritical fluid and liquid chromatographic separations, and particularly for analysis of enantiomeric and other stereoisomeric mixtures of various substances is shown.

Single arm attached cyclodextrin polysiloxanes and use thereof as chiral

Chiral copolymers containing chiral molecular grooves or cavities and oligosiloxane spacers are disclosed. The chiral portion of the copolymer is an enantiomerically enriched organic grouping, having physical properties attributed to uniform and stereochemically possible molecular grooves or cavities, which is chemically and thermally stable to gas, liquid or supercritical s fluid chromatographic conditions and is configured such that one enantiomer of an enantiomeric mixture will be better able to preferentially enter such groove or cavity and interact more strongly than other enantiomers in said mixture. The chiral grouping will contain one Or more combinations of organic moieties selected from the group consisting of methylene, phenylene, naphthylene, biphenylene, binaphthylene, a cyclodextrin and cycloalkylydene and substituted derivatives thereof and also includes non-metal atoms and functional groups which act as linking agents for the organic chiral cavity-containing moieties which are selected from the group consisting of ethers, thioethers, amines, carbonyls, amides, esters, sulfoxides, sulfonates, thioamides, thioesters, ureas, thioureas, carbamates, thiocarbamates, phosphines and phosphine oxides. The use of such polymers as chiral stationary phases in analytical and preparative gas, supercritical fluid and liquid chromatographic separations, and particularly for analysis of enantiomeric and other stereoisomeric mixtures of various substances is shown.

Chiral copolymers with oligosiloxane spacers

A chromatographic column, which has for a stationary phase a polysiloxane containing pendant cyano-substituted biphenyls, is selective in the chromatographic separation of organic compounds including polycyclic aromatic hydrocarbon isomers.

Polysiloxanes containing pendant cyano substituted biphenyls as

Disclosed herein is a class of chiral copper-amine complexes of the formula R(L*) CuLi in which L* is selected from: ##STR1## In this formula, R is a transferable ligand, which can be alkyl, aryl or aralkyl. M is a metal ion such as Li, Na, K, Cs, Rb, Be, Mg and other metal ions from the first two columns of the periodic table. R.sub.1 is straight chain alkyl, R.sub.2 is aryl or substituted aryl and R.sub.3 and R.sub.4 form a heterocyclic ring or a substituted heterocyclic ring with 4 to 8 members including oxygen and sulfur. Such complexes react with .alpha.,.beta.-unsaturated ketones, aldehydes, esters and other carbonyl containing compounds such that R is transferred to the 3 position enantioselectively as shown below. ##STR2## Such complexes react with .alpha.,.beta.-unsaturated ketones in the presence of trialkysilyl halides to give silyl enol ether in which R is substituted in the 3 position as shown below. ##STR3##

Chiral copper amine complexes

There is disclosed a catalytic hydrogenation process resulting in compounds of the formula ##STR1## wherein the dotted line represents a facultative bond, by hydrogenating the compound of the formula ##STR2## in the presence of a platinum or a nickel catalyst.

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Provo, UT, United States of America

Bryant E Rossiter