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Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones. | LitMetric
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Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.

Jacqueline H Smitrovich Geneviève N Boice Chuanxing Qu Lisa DiMichele Todd D Nelson Mark A Huffman Jerry Murry James McNamara Paul J Reider

Org Lett

Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065, USA.

Published: May 2002

[reaction: see text] The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-delta-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted delta-lactones.

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http://dx.doi.org/10.1021/ol0259847DOI Listing

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