By Prof. Dr. Mihaly Nogradi(auth.)
The state of the art in stereoselective synthesis!
completely revised and up to date, this enlarged moment version bargains a plethora of beneficial info on tools and reagents in stereoselective synthesis. tools were chosen for top potency and selectivity; mechanistic points are taken care of succinctly, with a powerful emphasis on functional functions. For this new version, fabric has been additional on
* homogeneous diastereoselective hydrogenations
* enantioselective oxidations
* novel, effective chiral auxiliaries
a lot of the data given is gifted in figures and tables, which makes the publication a priceless reference paintings for the virtually minded natural chemist.
From experiences of the 1st edition:
'The large fabric within the quantity should still end up rather priceless to someone enthusiastic about man made chemistry or educating a path in natural chemistry.' magazine of Medicinal Chemistry 'With approximately 1400 references stated, the e-book features a wealth of knowledge and may be an invaluable addition to the chemist's library.' the yankee Scientist
Content:
Chapter 1 basic ideas of Stereoselective Synthesis (pages 1–67):
Chapter 2 Stereoselective Catalytic savings (pages 45–80):
Chapter three Stereoselective Non?Catalytic discount rates (pages 81–121):
Chapter four Stereoselective Oxidations (pages 123–134):
Chapter five Stereoselective Carbon?Carbon Bond Forming Reactions via Nucleophilic Addition to Carbonyl teams (pages 135–211):
Chapter 6 Stereoselective Carbon?Carbon Bond Forming Reactions (pages 214–255):
Chapter 7 Stereoselective Carbon?Carbon Bond Formation by means of Pericyclic Reactions (pages 257–292):
Chapter eight Stereoselective Formation of Carbon?Heteroatom Bonds (pages 293–309):
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Extra info for Stereoselective Synthesis: A Practical Approach, Second Edition
Sample text
16-201. 1 Substrate Selectivity 0 t Tim k'+'>k'-' 15 cx) Fig. 1-7. Kinetic resolution as a function of time. builds up. This excess goes through a maximum and disappears on completion of the reaction (Fig. 1-7). If the reaction is interrupted before completion or if less than the necessary amount of reagent is applied, the result is a non-racemic mixture of the starting material and of a product in which an excess of the more reactive enantiomer of the substrate is incorporated. This way of partial separation of enantiomers is called kinetic resolution.
Regioselectivity arises from competition between groups (molecular sites) of different connectivity. An example is the chlorination of toluene which could lead, in principle, to four isomeric monochloro derivatives, of which practically only two (0 and p ) are formed. 1 Formation of Stereoisomers What we are really interested in is product stereoselectivity, a prerequisite for which is the fact that the formation of at least two stereoisomers from the same substrate should be possible. Therefore we should first examine the symmetry requirements for the formation of stereoisomers.
From a practical point of view we have to distinguish those cases when (i) the transformation rate of the less reactive enantiomer is virtually zero or (ii) when the two rates are comparable. So far the first case has been restricted to enzymatic transformations and was first exploited by Pasteur. He subjected racemic ammonium tartrate to fermentation with the mold Penicillium glaucum, whereby the unnatural ( - ) - ( 2 S , 3s) enantiomer remained unchanged and could be isolated. In recent years enzyme-catalyzed stereoselective transformations have become a powerful tool in preparative organic chemistry *.