Ephedrines

Aldrich ChemFiles 2005, 5.4, 9.

Aldrich ChemFiles 2005, 5.4, 9.

Both enantiomers of ephedrine, pseudoephedrine, norephedrine, and their derivatives are used as practical chiral auxiliaries for asymmetric synthesis. Enolates of readily available (1R,2R)-(–)- and (1S,2S)-(+)-pseudo-ephedrinepropionamide are substrates for diastereoselective alkylation reactions (Scheme 21), which after cleavage of the auxiliary, give rise to highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.1


Scheme 21

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Materials

     

References

  1. Myers, A. G. et al. J. Am. Chem. Soc. 1997, 119, 6496.

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