Sio 2 Books > Nonfiction 11 > Download e-book for kindle: Asymmetric Synthesis by R. A. Aitken (auth.), Dr R. Alan Aitken, Dr S. Nicholas

Download e-book for kindle: Asymmetric Synthesis by R. A. Aitken (auth.), Dr R. Alan Aitken, Dr S. Nicholas

By R. A. Aitken (auth.), Dr R. Alan Aitken, Dr S. Nicholas Kilényi (eds.)

ISBN-10: 9401045879

ISBN-13: 9789401045872

ISBN-10: 9401113467

ISBN-13: 9789401113465

1 Chirality.- 1.1 The phenomenon of chirality.- 1.2 The organic importance of chirality: the necessity for uneven synthesis.- 1.3 The selective synthesis of enantiomers.- 1.4 The enantiomeric purity of ordinary products.- 1.5 The stereogenic unit and kinds of chiral compound.- 1.6 Centrally chiral compounds of carbon and silicon.- 1.7 Centrally chiral compounds of nitrogen and phosphorus.- 1.8 Centrally chiral compounds of sulphur.- 1.9 Axially chiral compounds.- 1.10 Chiral molecules with a couple of stereogenic unit: diastereomers.- 1.11 The selective synthesis of diastereomers.- 1.12 Prochirality: enantotopic and diastereotopic groups.- 1.13 Absolute configuration 20 Reference and notes.- 2 the outline of stereochemistry.- 2.1 Compounds with one stereogenic centre.- 2.2 Axially chiral compounds.- 2.3 Compounds with multiple stereogenic unit.- 2.4 The topicity of enantioselective reactions.- 2.5 The relative topicity of diastereoselective reactions.- 2.6 additional issues on right terminology.- References and notes.- three Analytical tools: decision of enantiomeric purity.- 3.1 Polarimetric methods.- 3.2 fuel chromatography methods.- 3.3 Liquid Chromatographic methods.- 3.4 NMR spectroscopy.- 3.4.1 Chiral derivatising brokers (CDAs).- 3.4.2 Chiral solvating brokers (CSAs).- 3.4.3 Chiral lanthanide shift reagents (CLSRs).- 3.5 Concluding remarks.- References and notes.- four assets and techniques for the formation of chiral compounds.- 4.1 Chiral beginning materials.- 4.1.1 Amino acids and amino alcohols.- 4.1.2 Hydroxy acids.- 4.1.3 Alkaloids and different amines.- 4.1.4 Terpenes.- 4.1.5 Carbohydrates.- 4.2 equipment for the formation of chiral compounds.- 4.2.1 Use of clearly happening chiral compounds as development blocks.- 4.2.2 Resolution.- 4.2.3 equipment of uneven synthesis.- 4.2.4 particular methods.- 4.3 Mechanistic considerations.- References and notes.- five First- and second-generation equipment: chiral beginning fabrics and auxiliaries.- 5.1 Non-stereodifferentiating methods.- 5.1.1 Classical answer ((lR)-cis -permethric acid).- 5.1.2 answer utilizing a chiral auxiliary.- 5.1.3 Sulphoximines.- 5.1.4 equipment utilizing enantiomerically natural construction blocks.- 5.2 First-generation methods.- 5.2.1 Sugars.- 5.2.2 Amino acids.- 5.2.3 Terpenoids.- 5.2.4 Hydroxy acids.- 5.3 Second-generation equipment: nucleophiles bearing a chiral auxiliary.- 5.3.1 basic principles.- 5.3.2 Chiral enolate and aza-enolate equivalents.- 5.3.3 uneven aldol reactions.- 5.3.4 uneven ?-amino anions.- 5.3.5 Chiral sulphoxides.- 5.4 Electrophiles bearing chiral auxiliaries.- 5.4.1 uneven Michael additions.- 5.4.2 Chiral acetals.- 5.4.3 uneven additions to carbonyl compounds.- 5.5 Chiral auxiliaries in concerted reactions.- 5.5.1 Diels-Alder cycloaddition.- 5.5.2 The Claisen-Cope rearrangement.- References.- 6 3rd- and fourth-generation tools: uneven reagents and catalysts.- 6.1 C—C bond-forming reactions.- 6.1.1 uneven alkylation.- 6.1.2 uneven Michael reaction.- 6.1.3 uneven nucleophilic additions to carbonyl compounds.- 6.1.4 uneven [2 + 2] cycloadditions.- 6.1.5 uneven Diels-Alder reaction.- 6.1.6 Crotylboranes.- 6.1.7 uneven formation of alkene double bonds.- 6.2 Chiral acids and bases.- 6.3 uneven oxidation methods.- 6.3.1 uneven epoxidation of alkenes.- 6.3.2 uneven oxidation of sulphides.- 6.3.3 uneven dihydroxylation.- 6.3.4 Chiral oxaziridines and their uses.- 6.4 uneven relief, double bond isomerisation and hydroboration.- 6.4.1 Catalytic hydrogenation with chiral transition steel complexes.- 6.4.2 uneven double bond isomerisation.- 6.4.3 uneven hydroboration of alkenes.- 6.4.4 uneven aid utilizing chiral boranes and borohydrides.- 6.4.5 Chirally changed LiAlH4.- 6.5 Enzymatic and microbial methods.- 6.5.1 Enzymatic reduction.- 6.5.2 Enantioselective microbial oxidations.- 6.5.3 Esterases and lipases.- References.- 7 uneven overall synthesis.- 7.1 First-generation methods.- 7.1.1 (R)-(+)-Frontalin.- 7.1.2 (-)-Prostaglandin E1.- 7.1.3 The Merck synthesis of (+)-thienamycin.- 7.2 Second-generation methods.- 7.2.1 Prelog-Djerassi lactone.- 7.2.2 (R)-Muscone.- 7.2.3 (-)-Podophyllotoxin.- 7.2.4 (-)-Steganone.- 7.2.5 (+)-?-Allokainic acid.- 7.2.6 Leiobunum defence secretion.- 7.3 Third-generation methods.- 7.3.1 Carbocyclic iododeoxyuridine.- 7.4 Fourth-generation methods.- 7.4.1 A tricyclic analogue of indacrinone.- 7.4.2 (S)-(-)-Propranolol.- 7.4.3 Takasago (-)-menthol synthesis.- 7.4.4 (-)-Prostaglandin E1.- 7.4.5 Compactin and mevinolin analogues.- References.

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With several stereogenic units this becomes increasingly open to ambiguity however, and in these cases the relative configuration is probably better specified using the second system described below. As already mentioned, any term which only describes the relative configuration of the stereogenic units present actually applies to a pair of enantiomers and this forms the basis of a highly systematic way to specify relative configuration. This consists quite simply of choosing the enantiomer which has the R configuration in the first position and adding asterisks to its absolute configuration.

The absolute configuration of new chiral compounds can only be determined either by correlation with compounds of known configuration which can be traced back ultimately to an X-ray study or, if this is not possible, by making a new X-ray determination. References and notes 1. 1 2. A few examples are known in which the optical purity and the enantiomeric excess are not equivalent. e. by an independent method in addition to polarimetry (see chapter 3). 3. A. E. Maryanoff in Asymmetric Synthesis, Vol.

The first is the stereochemically dependent position of groups with large magnetic anisotropy, such as phenyl rings and carbonyl functions, relative to other substituents in each of the solvate complexes. The second is the relative magnitude of the solvation constants KR and Ks for the solute enantiomers. Exchange between the chiral and achiral solvates is rapid on the NMR timescale. ()s where R and s are the fractional populations of achiral solvates. ()± The advantage of the CSA technique is that it is quick and simple, requiring no separate derivatising reaction prior to NMR assay.

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Asymmetric Synthesis by R. A. Aitken (auth.), Dr R. Alan Aitken, Dr S. Nicholas Kilényi (eds.)

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