Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones |
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| Authors: | Smitrovich Jacqueline H Boice Geneviève N Qu Chuanxing DiMichele Lisa Nelson Todd D Huffman Mark A Murry Jerry McNamara James Reider Paul J |
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| Institution: | Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065, USA. jacqueline_smitrovich@merck.com |
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| Abstract: | 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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