Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.
[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.
Smitrovich
Jacqueline H
JH
Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065, USA. jacqueline_smitrovich@merck.com
Boice
Geneviève N
GN
Qu
Chuanxing
C
DiMichele
Lisa
L
Nelson
Todd D
TD
Huffman
Mark A
MA
Murry
Jerry
J
McNamara
James
J
Reider
Paul J
PJ
D002384:Catalysis; D018360:Crystallography, X-Ray; D004809:Ephedrine / Q000737:chemistry*; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007783:Lactones; D004809:Ephedrine