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Encyclopedia > Diastereoselectivity
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Diastereomers are stereoisomers that are not enantiomers or mirror images of each other. Diastereomers can have different physical properties and different reactivity. Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ... In chemistry two stereoisomers are said to be enantiomers if they are mirror images of each other. ...


If a molecule contains a single asymmetric carbon atom, it will have two mirror image forms. If a molecule contains two asymmetric carbons, there are 4 possible configurations, and they can not all be mirror images of each other. The possibilities continue to multiply as there are more asymmetric centers in a molecule. Jump to: navigation, search A molecule is the smallest particle of a pure chemical substance that still retains its chemical composition and properties. ... Jump to: navigation, search General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Jump to: navigation, search Properties For alternative meanings see atom (disambiguation). ...


Tartaric acid contains two asymmetric centers, but two of the configurations are equivalent and together are called meso compounds. This configuration is not optically active, while the remaining two configurations are d- and l- mirror images. The meso form is a diastereomer of the other forms. Tartaric acid is a white crystalline organic acid. ... Meso compound is a chemical compound whose molecules contain asymmetric centers but which is optically inactive due to overall symmetry. ... When polarized light is passed through a substance containing chiral molecules (or nonchiral molecules arranged asymmetrically), the direction of polarization can be changed. ...


The families of 5 and 6 carbon carbohydrates contain many diastereomers because of the large numbers of asymmetric centers in these molecules. Jump to: navigation, search Carbohydrates (literally hydrates of carbon) are chemical compounds that consist of monosaccharide sugars of varying chain lengths and that have the general chemical formula Cm(H2O)n or are derivatives of such. ...


Two common prefixes used to distinguish diastereomers are threo and erythro. When drawn in the Fischer projection the erythro isomer has two identical substituents on the same side and the threo isomer has them on opposite sites. Jump to: navigation, search Fischer projection of D-glucose In chemistry (particularly organic chemistry and biochemistry), a Fischer projection is a two-dimensional representation of a three-dimensional organic molecule by projection. ...


Diastereoselectivity is the preference for the formation of one or more than one diastereomer over the other in an organic reaction. Organic reactions are chemical reactions between organic compounds. ...


  Results from FactBites:
 
Assymetric Induction (8654 words)
BH, the diastereoselectivity is reversed, with isomer B being formed in 82% de.
Its use in the reduction of 2,6-dimethyl-5-hydroxy-3-heptanone produces excellent diastereoselectivity, as a consequence of the intramolecular hydride transfer intermediate drawn in the right green shaded box (the bulky R substituent prefers to occupy an equatorial-like position).
The increased diastereoselectivity of the Mukaiyama aldol reaction is noteworthy (de is 92 versus 56 for the analogous case in equation 1), and reflects the open transition state adopted by this reaction.
Stereoselective Additions To Alpha-Beta-Epoxyaldehydes (1090 words)
The observation of any useful level of diastereoselectivity in the addition of simple nucleophiles to trans-substituted alpha-beta-epoxyaldehydes was unexpected, given the lack of diastereoselectivity found when a C-substituent replaces the silyl group.
Nevertheless, the sense of the diastereoselectivity observed in additions to 1 and 2 is consistent with a `non-chelation' model, similar to the working hypothesis in our group used to account for the results from cis-alpha-beta-epoxyaldehydes.
It appears that the preceding modelling and results from measurements in the solid state are not inconsistent with the suggestion outlined in Figure 3 that dipole-dipole repulsion is a significant factor in determining the minimum energy conformation of alpha-beta-epoxyaldehydes of this type.
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