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Chiral auxiliary
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions / From Wikipedia, the free encyclopedia
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In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis.[1][2] The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use.
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Most biological molecules and pharmaceutical targets exist as one of two possible enantiomers; consequently, chemical syntheses of natural products and pharmaceutical agents are frequently designed to obtain the target in enantiomerically pure form.[3] Chiral auxiliaries are one of many strategies available to synthetic chemists to selectively produce the desired stereoisomer of a given compound.[4]
Chiral auxiliaries were introduced by Elias James Corey in 1975[5] with chiral 8-phenylmenthol and by Barry Trost in 1980 with chiral mandelic acid. The menthol compound is difficult to prepare and as an alternative trans-2-phenyl-1-cyclohexanol was introduced by J. K. Whitesell in 1985.