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A given stereocenter has two possible configurations (R and S), which give rise to stereoisomers (diastereomers and enantiomers) in molecules with one or more stereocenter. For a chiral molecule with one or more stereocenter, the enantiomer corresponds to the stereoisomer in which every stereocenter has the opposite configuration.
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. [1] The study of stereochemistry focuses on the relationships between stereoisomers, which are defined as having the same molecular formula and sequence of bonded atoms (constitution) but differing in the geometric positioning of the atoms in space.
Chiral auxiliaries are incorporated into synthetic routes to control the absolute configuration of stereogenic centers. David A. Evans' synthesis of the macrolide cytovaricin, considered a classic, utilizes oxazolidinone chiral auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting the absolute stereochemistry of nine stereocenters.
The racemization occurs by way of an intermediate enol form in which the former stereocenter becomes planar and hence achiral. [14]: 373 An incoming group can approach from either side of the plane, so there is an equal probability that protonation back to the chiral ketone will produce either an R or an S form, resulting in a racemate.
A molecule having exactly one chiral stereocenter (usually an asymmetric carbon atom) can be labeled (R) or (S), but a molecule having multiple stereocenters needs more than one label. For example, the essential amino acid L-threonine contains two chiral stereocenters and is written (2S,3S)-threonine.
Enantiotopic groups are identical and indistinguishable except in chiral environments. For instance, the CH 2 hydrogens in ethanol (CH 3 CH 2 OH) are normally enantiotopic, but can be made different (diastereotopic) if combined with a chiral center, for instance by conversion to an ester of a chiral carboxylic acid such as lactic acid, or if coordinated to a chiral metal center, or if ...
A Fischer projection can be used to differentiate between L- and D- molecules Chirality (chemistry). For instance, by definition, in a Fischer projection the penultimate carbon of D-sugars are depicted with hydrogen on the left and hydroxyl on the right. L-sugars will be shown with the hydrogen on the right and the hydroxyl on the left.
A chiral molecule is a type of molecule that has a non-superposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom. [16] [17] The term "chiral" in general is used to describe the object that is non-superposable on its mirror image. [18]