Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones

AG Myers, BH Yang, H Chen, L McKinstry…

Index: Myers, Andrew G.; Yang, Bryant H.; Chen, Hou; McKinstry, Lydia; Kopecky, David J.; Gleason, James L. Journal of the American Chemical Society, 1997 , vol. 119, # 28 p. 6496 - 6511

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Citation Number: 536

Abstract

The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted ...